Ethyl 4-bromobutyrate → Ethyl 4-(3-piperidinomethylphenoxy)butyrate

HRID 485378Notes

Reaction equation

HRID 485378 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[O:14][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 76300Ethyl 4-bromobutyrateHCID 8269741-(3-Hydroxybenzyl)piperidine

Product 1

HCID 14221804Ethyl 4-(3-piperidinomethylphenoxy)butyrateYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(1-piperidinylmethyl)phenol (11.2 g) sodium hydride (1.5 g) and ethyl 4-bromobutyrate (11.7 g) in dimethylformamide (60 ml) was stirred at 25° during 20 h. The mixture was poured onto ice (300 g) and extracted with ethyl acetate (3×100 ml). The combined extracts were distilled to give the title compound as a colourless oil (16.9 g) b.p. 250°, 0.1 mm; tlc System B, Rf 0.9.

Workup

  1. additionThe mixture was poured onto ice (300 g)
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. distillationThe combined extracts were distilled

Sources & evidence

ORD record
ord-58e532b6da564ca1adf70bcc6f7a79d0
Source dataset
uspto-grants-1985_08
Patent number
US04536508

Reaction notes

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