3-Hydroxyphenacyl bromide → N-[4-[2-[[6-[[2-(3-Hydroxyphenyl)-2-oxoethyl](phenylmethyl)amino]hexyl]oxy]ethyl]phenyl]acetamide

HRID 1165279Notes

Reaction equation

HRID 1165279 reaction equation
[C:1]1([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([OH:38])[CH:33]=1)=[O:31]>ClCCl.O>[OH:38][C:34]1[CH:33]=[C:32]([C:30](=[O:31])[CH2:29][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:22][CH:23]=2)[CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 2

HCID 69172063-Hydroxyphenacyl bromideHCID 20062786N-[4-[2-[[6-[(phenylmethyl)amino]hexyl]oxy]ethyl]phenyl]acetamide

Product 1

HCID 19862714N-[4-[2-[[6-[[2-(3-Hydroxyphenyl)-2-oxoethyl](phenylmethyl)amino]hexyl]oxy]ethyl]phenyl]acetamideYield 52.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-[4-[2-[[6-[(phenylmethyl)amino]hexyl]oxy]ethyl]phenyl]acetamide (1 g), 2-bromo-1-(3-hydroxyphenyl)ethanone (0.61 g) and DEA (0.8 g) in dichloromethane (20 ml) was stirred under nitrogen for 18 h, diluted with water (20 ml), and extracted with dichloromethane (25 ml). The organic layer was washed with 8% sodium bicarbonate solution (20 ml), dried and evaporated in vacuo to give the title compound as a yellow oil (0.71 g).

Workup

  1. extractionextracted with dichloromethane (25 ml)
  2. washThe organic layer was washed with 8% sodium bicarbonate solution (20 ml)
  3. customdried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-f68b0d3099ed4a979dc1a5cf721f00ee
Source dataset
uspto-grants-1990_03
Patent number
US04908386

Reaction notes

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