Triethylamine → 1-[1(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropyl}-4-methylbenzamide

HRID 1250540Notes

Reaction equation

HRID 1250540 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][CH:23](N)[CH:24]([CH3:26])[CH3:25])[CH2:18][CH2:17]1.C([N:34](CC)CC)C>ClCCl>[Cl:11][C:12]1[CH:13]=[C:14]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][CH:23]([C:4]2([CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH2:3]2)[C:7]([NH2:34])=[O:8])[CH:24]([CH3:26])[CH3:25])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 222576661(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropylamine

Product 1

HCID 865889811-[1(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropyl}-4-methylbenzamideYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Toluoyl chloride (0.077 ml, 0.58 mmol) was added to a solution of 1(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropylamine(0.16 g, 0.49 mmol) in dichloromethane (2 ml) and triethylamine (0.12 ml, 1.63 mmol). The reaction mixture was stirred at room temperature for 1.5 h and was quenched with water. The product was then extracted with dichloromethane and the organic layer was washed with brine and dried over sodium sulfate. The crude product was purified on preparative TLC with 25% acetone, 25% dichloromethane in hexanes to give 0.21 g of N-{1-[1(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropyl}-4-methylbenzamide as an oil, which was then converted to its dihydrochloride salt (0.15 g); m.p. 233.9-235.5° C.

Workup

  1. customwas quenched with water
  2. extractionThe product was then extracted with dichloromethane
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe crude product was purified on preparative TLC with 25% acetone, 25% dichloromethane in hexanes

Sources & evidence

ORD record
ord-82d7a23f7d354c76b3b5ac7039121917
Source dataset
uspto-grants-2002_01
Patent number
US06339087B1

Reaction notes

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