Benzoyl chloride → N-(1-(Benzyl)-4-piperidyl)benzamide

HRID 1066983Notes

Reaction equation

HRID 1066983 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl.O>[CH2:8]([N:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:3][CH2:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 40598N-(1-(Benzyl)-4-piperidyl)benzamideYield 87.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a biphasic solution of 4-amino-1-benzylpiperidine (6.0 g, 31.6 mmol), K2CO3 (8.71 g, 63.1 mmol) in CH2Cl2 (200 mL) and water (100 mL) was added benzoyl chloride (4.86 g, 34.7 mmol) in 20 mL of CH2Cl2 at 0° C. with stirring. After stirring for 4 h at room temperature, the layers were separated. The organic layer was washed with water, dried over MgSO4 and filtered. The solvent was removed in vacuo to obtain 1-benzyl-4-benzamidopiperidine (8.16 g, 87% yield) as a white solid. It was used in the next step without purification.

Workup

  1. stirringAfter stirring for 4 h at room temperature
  2. customthe layers were separated
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7aa16512fe6d405aa32028c1a7a3ebf4
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

Loading…