Benzaldehyde → HCID 69809311, compound

HRID 1809471Notes

Reaction equation

HRID 1809471 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH3-]C#N.[Na+]>CO>[CH2:14]([N:10]1[CH2:11][CH2:12][CH2:13][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:9]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 203645753-(4-Chlorophenyl)piperidine

Product 1

HCID 69809311HCID 69809311, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(4-chlorophenyl)piperidine in MeOH (0.2 M), benzaldehyde (2.1 eq.) was added and the reaction mixture was stirred at RT for 1 h. Then, it was cooled to 0° C. and NaBH3CN (3 eq.) was added. The mixture was allowed to warm to RT and stirred for 1 h. Evaporation of the solvent gave a residue that was partitioned between sat. aq. NaHCO3 and EtOAc and the organic phase was separated and dried (Na2SO4). Evaporation of the solvent gave a crude that was purified by flash chromatography column on silica (Petroleum ether to EtOAc/Petroleum ether 1:19) yielding (62%) the title compound as a yellow powder. 1H NMR (300 MHz, DMSO-d6, 300K) δ 7.36-7.17 (9H, m), 3.48 (2H, s), 2.87-2.68 (3H, m), 2.05-1.91 (2H, m), 1.86-1.75 (1H, m), 1.74-1.50 (2H, m), 1.48-1.3 (1H, m). MS (ES+) C18H20ClN required: 285, found: 286 (M+H)+.

Workup

  1. temperatureThen, it was cooled to 0° C.
  2. temperatureto warm to RT
  3. stirringstirred for 1 h
  4. customEvaporation of the solvent
  5. customgave a residue that
  6. customwas partitioned between sat. aq. NaHCO3 and EtOAc
  7. customthe organic phase was separated
  8. dry with materialdried (Na2SO4)
  9. customEvaporation of the solvent
  10. customgave a crude that
  11. customwas purified by flash chromatography column on silica (Petroleum ether to EtOAc/Petroleum ether 1:19)

Sources & evidence

ORD record
ord-4649d5edcdd6477f9b34ba6019c8ea3c
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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