Reaction SMILES: [C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1>C1COCC1>[C:2]1([C:1]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([OH:8])[CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: CN1CCC(Cl)CC1
Reactant: O=C(c1ccccc1)c1ccccc1
Solvent: C1CCOC1
Product: CN1CCC(C(O)(c2ccccc2)c2ccccc2)CC1
Reaction time: 8 h

Procedure:
A solution of benzophenone (60 g, 0.33 mol) in anhydrous THF (200 mL) was added dropwise over a period of 20 min to a Grignard reagent that was prepared from 59 g (0.44 mol) of freshly distilled 4-chloro-1-methylpiperidine, Mg (1.3 mol) in THF (1L). After stirring overnight, the reaction mixture was quenched (H2O, then dilute HCl) and extracted (2×500 mL) with ethyl acetate. The combined organics were dried with Na2SO4, filtered, and evaporated to dryness to give 89.5 g of alcohol 9. This alcohol was used without further purification. The structure was confirmed by 1H NMR. 4-(Diphenylmethylidene)-1-methylpiperidine (10). Alcohol 9 (27.3 g, 97 mmol) was suspended in concentrated HCl (360 mL) and heated at reflux (oil bath temperature above 96° C.) for 2 h. The mixture was cooled in an ice bath followed by the addition of ethyl acetate (300 mL). A solution of sodium hydroxide (200 g) in water (400 mL), cooled to 10° C., was added dropwise to the acidic mixture until the pH was 14. Ethyl acetate (200 mL) was then added and the organic layer was separated and washed with brine (200 mL). The combined aqueous layers were extracted with ethyl acetate (2×300 mL). The combined organic layers were dried, filtered, and concentrated to give 23 g of the product as a brown oil. 1H NMR confirmed the structure of the product. 4-(Diphenylmethyl)-1-methylpiperidine (12). Solid sodium borohydride (6 g, 160 mmol) and solid alcohol 9 (4.5 g, 16 mmol) were mixed to a fairly homogeneous solid mixture using a spatula. With rapid N2 flow through the system, the solid mixture was added intermittently (cautiously and in small portions over a period of 45 min) to stirred trifluoroacetic acid (200 mL) cooled to 0° C. Extra caution was taken during the addition of the NaBH4 mixture to prevent localized heating and rapid build-up of pressure from the evolving and highly flammable H2. After the addition was complete, the reaction mixture was evaporated to dryness. The above procedure was repeated using 5.2 g of 9 and proportional amounts of the other reagents. The combined residues from the two experiments were diluted with EtOAc/CH2Cl2 followed by the addition of aqueous NaOH and then solid NaOH until the aqueous layer maintained a pH of 11. The organic layer was dried with Na2SO4, filtered, and evaporated to an oil that solidified. Chromatography over silica gel using 10% MeOH/10% Et3N in EtOAc gave 6.75 g of 12 as a white crystalline solid. 1-ethoxycarbonyl 4-(diphenylmethylidene)piperidine (19). Alkene-amine 10 (23 g) was suspended in toluene (150 mL), whereupon dry potassium carbonate (13 g) was added. The mixture was then stirred for 15 minutes, filtered, and the filtrate concentrated to yield 18.5 g of purified 1-methyl 4-(diphenylmethylidene)-piperidine. This purified material was dissolved in dry toluene (100 mL), whereupon dry potassium carbonate (38 g, 275 mmol) was added. Ethyl chloroformate (26.7 g, 245 mmol, 3.5 equiv.) was added slowly with stirring and the mixture was heated at reflux overnight. The reaction mixture was cooled to room temperature and the mixture was then filtered. The reaction vessel and filter cake were subsequently washed with toluene (50 mL) and the filtered solid was then partitioned between water (125 mL) and ethyl acetate (100 mL). Stirring was required to dissolve the potassium carbonate within the solid and the layers were subsequently separated. The organic layer was dried with Na2SO4, filtered, and concentrated to yield 2.9 g of starting amine. The toluene layer obtained from washing the reaction vessel and the filter cake was dried with Na2SO4, filtered, concentrated, and the residue purified by flash chromatography (5/1 heptane/EtOAc) to yield 11.47 g (51%) of 19. 1H NMR confirmed the structure of the product and the starting amine. (Carbamate 21 was similarly prepared.) 4-(diphenylmethylidene)piperidine (20). Sodium hydroxide (15.85 g, 396 mmol) in water (30 mL) was added to the carbamate 1-ethoxycarbonyl 4-(diphenylmethylidene)piperidine 19 (11.47 g, 35.7 mmol) dissolved in ethanol (150 mL). The mixture was heated at reflux overnight. The reaction mixture was cooled to room temperature was then partitioned between water (100 mL) and ethyl acetate (150 mL). The mixture was stirred to dissolve the solid and the layers were separated. The organic layer was washed with brine (100 mL) and the separate aqueous layers were extracted with ethyl acetate (100 mL). The combined organic layers were dried with Na2SO4, filtered, and concentrated. The yellow oil was dried by high vacuum to give 6.7 g (75%) of 20 as a yellow-white waxy solid. 1H NMR was used to confirm the structure of the product. (Amine 22 was similarly prepared.)