Benzaldehyde → 1-{[(3S)-1-Benzylpiperidin-3-yl]methyl}-N-(3,4-dichlorophenyl)piperidine-4-carboxamide

HRID 603236Notes

Reaction equation

HRID 603236 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:25]([N:21]1[CH2:22][CH2:23][CH2:24][C@@H:19]([CH2:18][N:15]2[CH2:14][CH2:13][CH:12]([C:10]([NH:9][C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)=[O:11])[CH2:17][CH2:16]2)[CH2:20]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 57656947N-(3,4-dichlorophenyl)-1-[(3R)-piperidin-3-ylmethyl]piperidine-4-carboxamide

Product 1

HCID 117195521-{[(3S)-1-Benzylpiperidin-3-yl]methyl}-N-(3,4-dichlorophenyl)piperidine-4-carboxamideYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-(3,4-dichlorophenyl)-1-[(3R)-piperidin-3-ylmethyl]piperidine-4-carboxamide (150 mg) and benzaldehyde (0.04 mL) in dichloromethane was added sodium triacetoxyborohydride (103 mg). The reaction mixture was stirred at room temperature for 18 hours. The reaction was incomplete so sodium triacetoxyborohydride (50 mg) was added and the mixture was stirred for 48 hours. The reaction mixture was partitioned between dichloromethane and water and the organic layer was washed with brine. The organic extract was dried over magnesium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in dichloromethane to give the title compound as a white solid (28 mg, 15%)

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 48 hours
  3. customThe reaction mixture was partitioned between dichloromethane and water
  4. washthe organic layer was washed with brine
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by silica column chromatography
  9. washeluting with a gradient of 0 to 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-88956684dc1542d7b17e1cd4978f07ef
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

Loading…