Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH2:1]1[O:3][C@@H:2]1[CH2:4]O.[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(CCO)CC>C1COCC1>[O:3]1[CH2:1][C@H:2]1[CH2:4][N:10]1[C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]2[C:6]1=[O:16]
Reactant: OC[C@@H]1CO1
Reactant: O=C1NC(=O)c2ccccc21
Agent: CCN(CC)CCO
Agent: c1ccc(P(c2ccccc2)c2ccccc2)cc1
Solvent: C1CCOC1
Product: O=C1c2ccccc2C(=O)N1C[C@@H]1CO1
Reaction time: 8 h
Yield: 75.4 %

Procedure:
To THF solution (400 ml) of (R)-(+)-glycidol 2.47 g (32 mmol), phthalimide 7 g (47.6 mmol), triphenyl phosphine 14.3 g (54.5 mmol) and molecular shieve 4 Å 30 g were added at room temperature and then DEAE 8.7 g (50 mmol) was added dropwise under cooling on ice-bath. The reaction mixture was allowed to stand at room temperature overnight. Molecular shieve was removed by filtration and filtrate was evaporated to dryness in vacuo. The desired product was further purified by silica gel chromatography. 4.9 g of desired product was obtained as an oil. The NMR spectra were consistent with the desired title intermediate.
Reaction SMILES: [C:1]([CH:5]1[C:10](=[O:11])[CH2:9][CH:8]([CH2:12][CH:13]([S:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[CH3:14])[CH2:7][C:6]1=[O:26])(=O)[CH2:2][CH3:3].Cl.[CH2:28]([O:30][NH2:31])[CH3:29].C(N(CC)C1C=CC=CC=1)C.O>C(OCC)(=O)C>[CH2:28]([O:30][NH:31][C:1](=[C:5]1[C:10](=[O:11])[CH2:9][CH:8]([CH2:12][CH:13]([S:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:18][CH:17]=2)[CH3:14])[CH2:7][C:6]1=[O:26])[CH2:2][CH3:3])[CH3:29]
Reactant: CCC(=O)C1C(=O)CC(CC(C)Sc2ccc(C(F)(F)F)cc2)CC1=O
Reactant: CCON
Agent: Cl
Solvent: CCN(CC)c1ccccc1
Solvent: CCOC(C)=O
Solvent: O
Product: CCONC(CC)=C1C(=O)CC(CC(C)Sc2ccc(C(F)(F)F)cc2)CC1=O
Temperature: 25 °C

Procedure:
0.27 Gram of 2-propionyl-5-[2-(4-trifluoromethylphenylthio)propyl]cyclohexane-1,3-dione was dissolved in 10 ml of ethyl acetate, and 0.08 g of ethoxyamine hydrochloride and 0.1 g of N,N-diethylaniline were added to the resulting solution which was then refluxed for 5 hours. The reaction solution was cooled to room temperature, poured into water, weakly acidified and extracted with ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid and water subsequently and dried over anhydrous magnsium sulfate. After removing ethyl acetate, the residue was purified by thin layer chromatography (eluent, hexane:ethyl acetate=5:1) to obtain 0.13 g of 2-(1-ethoxyaminopropylidene)-5-[2-(4-trifluoromethylphenylthio)propyl]cyclohexane-1,3-dione.
Reaction SMILES: NC1CC[N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)CC1.C(N(CC)CC)C.ClC(OC[C:27]1[CH:32]=[CH:31]C=[CH:29][CH:28]=1)=O>O1CCCC1>[CH3:29][CH2:28][CH2:27][CH2:32][CH2:31][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:9][CH2:8][NH2:5]
Reactant: NC1CCN(Cc2ccccc2)CC1
Reactant: O=C(Cl)OCc1ccccc1
Solvent: CCN(CC)CC
Solvent: C1CCOC1
Product: CCCCCCCCCCCCN
Temperature: 25 °C
Reaction time: 12 h
Yield: 69.3 %

Procedure:
To a 0° C. solution of 4-amino-1-benzylpiperidine 11 (41.2 g, 216.5 mmol) and triethylamine (51.3 mL, 369 mmol) in 600 mL of tetrahydrofuran was added benzyl chloroformate (31 mL, 217 mmol) dropwise over a period of 30 to 45 min. at such a rate that the reaction temperature was kept between 5° C. and 10° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature and stir for 12 hours. The solvent and volatiles were removed under reduced pressure. Water (500 mL) and ethyl acetate (1.2 L) were then added and the reaction was partitioned between the two phases. The organic layer was washed with saturated aqueous sodium bicarbonate solution (2×, 150 mL) and then dried (brine, MgSO4). Evaporation of the solvent yielded a tan liquid which was purified via column chromatography (SiO2, EtOAc/Hexane—30/70 to EtOAc—100) to provide 27.8 g of the amine 12 as a white solid (mass spec. M+=324, MP=79.1-79.6° C.).