Dimethylformamide → (2-Hydroxy-4-methoxyphenyl)[1-(phenylmethyl)-4-piperidinyl]methanone

HRID 223561Notes

Reaction equation

HRID 223561 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+].CN(C)C=O>O>[CH2:18]([N:9]1[CH2:8][CH2:7][CH:6]([C:4](=[O:5])[C:3]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:2]=2[OH:1])[CH2:11][CH2:10]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 13076390(2-Hydroxy-4-methoxyphenyl)(piperidin-4-yl)methanone

Product 1

HCID 13076397(2-Hydroxy-4-methoxyphenyl)[1-(phenylmethyl)-4-piperidinyl]methanoneYield 57.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.50 g of 4-(2-hydroxy-4-methoxybenzoyl)piperidine, 6.40 ml of benzyl bromide, 10.20 g of sodium bicarbonate and 74.0 ml of dimethylformamide was stirred at 60° for 15 hrs. The reaction mixture was poured into 250 ml of water and a precipitate formed. The precipitate was collected, washed with water and recrystallized from ethanol to yield 10.0 g (57.4%) of product, mp, 123°-125°.

Workup

  1. customa precipitate formed
  2. customThe precipitate was collected
  3. washwashed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8f9529d8ef5e4457b46d17226a4d7726
Source dataset
uspto-grants-1982_10
Patent number
US04355037

Reaction notes

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