Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: F[P-](F)(F)(F)(F)F.[CH3:8][N+:9](C)=[C:10](N(C)C)ON1C2N=CC=CC=2N=N1.[C:25]([O:29][C:30]([NH:32][C@@H:33]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH:45]([CH3:47])[CH3:46])=[CH:40][CH:39]=1)[C:34](O)=[O:35])=[O:31])([CH3:28])([CH3:27])[CH3:26].C(N(CC)C(C)C)(C)C.CNC.O1CCCC1>CN(C)C=O>[CH3:8][N:9]([CH3:10])[C:34](=[O:35])[C@@H:33]([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH:45]([CH3:47])[CH3:46])=[CH:40][CH:39]=1
Reactant: CC(C)Oc1ccc(C[C@H](NC(=O)OC(C)(C)C)C(=O)O)cc1
Reactant: CN(C)C(On1nnc2cccnc21)=[N+](C)C
Agent: CNC
Agent: F[P-](F)(F)(F)(F)F
Solvent: C1CCOC1
Solvent: CCN(C(C)C)C(C)C
Solvent: CN(C)C=O
Product: CC(C)Oc1ccc(C[C@H](NC(=O)OC(C)(C)C)C(=O)N(C)C)cc1
Reaction time: 0.17 h
Yield: 71.3 %

Procedure:
N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (88 mg, 0.23 mmol) was added to a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-isopropoxyphenyl)propanoic acid (50 mg, 0.2 mmol) in N,N-dimethylformamide (5 mL) and N,N-diisopropylethylamine (54 uL, 0.31 mmol). The reaction was stirred for 10 min, and the 2.00 M of dimethylamine in tetrahydrofuran (0.4 mL, 0.6 mmol) was added. The reaction was stirred for 2 h. at r.t. and was partitioned between water and ethyl acetate. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product, (S)-tert-butyl 1-(dimethylamino)-3-(4-isopropoxyphenyl)-1-oxopropan-2-ylcarbamate (50 mg, 90%). Analytical LCMS (M+H-Boc)+: m/z=251.0.
Reaction SMILES: [F:1][C:2]([F:25])([F:24])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:25][C:2]([F:1])([F:24])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:9][CH:10]=1
Reactant: CC(C)(C)OC(=O)N1CCN(c2ccc(OCC(F)(F)F)cc2)CC1
Solvent: O=C(O)C(F)(F)F
Solvent: ClCCl
Product: FC(F)(F)COc1ccc(N2CCNCC2)cc1
Temperature: 25 °C
Reaction time: 8 h
Yield: 90.9 %

Procedure:
Crude tert-butyl 4-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine-1-carboxylate (32.47 g, approx 57 mmol) was dissolved in DCM (300 ml) and TFA (69 mL) was added. The reaction was stirred at room temperature overnight then evaporated to dryness, azeotroping with toluene. The residue was partitioned between DCM and saturated sodium bicarbonate solution. The organic phase was separated, dried (MgSO4), filtered and concentrated to yield 1-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine as a solid (13.48 g, 91%)
Reaction SMILES: [OH:1][CH2:2][CH2:3][C:4]1[CH:23]=[CH:22][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.[CH:24]1[C:29](O)=[CH:28][CH:27]=[C:26]([CH3:31])[CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1.C1COCC1>[CH3:31][C:26]1[CH:27]=[CH:28][C:29]([O:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([CH2:8][N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:11][CH2:10]3)=[CH:22][CH:23]=2)=[CH:24][CH:25]=1
Reactant: Cc1ccc(O)cc1
Reactant: CC(C)(C)OC(=O)N1CCN(Cc2ccc(CCO)cc2)CC1
Agent: CCOC(=O)/N=N/C(=O)OCC
Agent: c1ccc(P(c2ccccc2)c2ccccc2)cc1
Solvent: Cc1ccccc1
Solvent: C1CCOC1
Product: Cc1ccc(OCCc2ccc(CN3CCN(C(=O)OC(C)(C)C)CC3)cc2)cc1
Temperature: 25 °C
Reaction time: 85 h
Yield: 63.7 %

Procedure:
To a THF (40 mL) solution of tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate (4.74 g) and p-cresol (1.76 g) were added triphenylphosphine (4.27 g) and 2.2 M solution of DEAD in toluene (7.40 mL) at 0° C. After stirring at room temperature for 85 hours, the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=3/1 to 1/2), then the concentrated eluate was diluted with CH2Cl2, and washed with 5 M NaOH and saturated aqueous NaCl, dried over anhydrous MgSO4, and concentrated under reduced pressure to give tert-butyl 4-{4-[2-(4-methylphenoxy)ethyl]benzyl}piperazine-1-carboxylate as a yellow solid (3.87 g).
Reaction SMILES: [F:1][C:2]([F:20])([F:19])[C:3]1[C:13]2[S:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[NH:9][C:8](=[O:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[CH3:23]I>CN(C=O)C>[CH3:23][N:9]1[C:8](=[O:18])[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:19])[F:20])[C:13]=2[S:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]1=2
Reactant: O=C1Nc2ccccc2Sc2c1cccc2C(F)(F)F
Reactant: CI
Agent: [H-]
Agent: [Na+]
Solvent: CN(C)C=O
Product: CN1C(=O)c2cccc(C(F)(F)F)c2Sc2ccccc21
Reaction time: 1 h

Procedure:
To a solution of 4-trifluoromethyl-10,11-dihydrodibenzo[b,f][1,4]thiazepin-11-one (0.295 g, 1 mmol) in DMF (20 ml) was added sodium hydride (0.1 g of 60% dispersion in oil) and the resulting mixture stirred for 30 minutes, before methyl iodide (1 equivalent) was added. After stirring for 1 hour the mixture was evaporated and the residue separated between ethyl acetate and aqueous sodium bicarbonate. The organic fractions were dried (magnesium sulphate) and evaporated. Purification of the residue by chromatography on silica, eluting with ethyl acetate/petrol (1:1, v/v), followed by recrystallisation from cyclohexane gave the title compound as colourless needles (0.121 g, m.p. 139°-141°, Rf 0.41 [silica, ethyl acetate/petrol, 1:2, v/v]).
Reaction SMILES: Br[C:2]1[CH:3]=[CH:4][C:5]2[O:24][CH2:23][C:8]3([C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]3=[O:22])[C:6]=2[CH:7]=1.Br[C:26]1[CH:31]=[CH:30][C:29]2C3(C[O:48][C:28]=2[CH:27]=1)C1C(=CC=CC=1)N(CCCCC)C3=O>>[CH2:17]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]2([C:6]3[CH:7]=[C:2]([O:48][C:28]4[CH:29]=[CH:30][CH:31]=[CH:26][CH:27]=4)[CH:3]=[CH:4][C:5]=3[O:24][CH2:23]2)[C:9]1=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21]
Reactant: CCCCCN1C(=O)C2(COc3cc(Br)ccc32)c2ccccc21
Reactant: CCCCCN1C(=O)C2(COc3ccc(Br)cc32)c2ccccc21
Product: CCCCCN1C(=O)C2(COc3ccc(Oc4ccccc4)cc32)c2ccccc21
Yield: 10 %

Procedure:
Following the procedure as described in EXAMPLE 36, and making non-critical variations using 5-bromo-1′-pentylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 6-bromo-1′-pentylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, the title compound was obtained (10% yield) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.32-7.10 (m, 5H), 7.06-6.82 (m, 6H), 6.42 (d, 1H), 4.95 (d, 1H), 4.71 (d, 1H), 3.82-3.62 (m, 2H), 1.75-1.63 (m, 2H), 1.43-1.34 (m, 4H), 0.85 (t, 3H); MS (ES+) m/z 400.4 (M+1).