4-Bromobutyronitrile → 4-{3-[(Piperidin-1-yl)methyl]phenoxy}butanenitrile

HRID 485374Notes

Reaction equation

HRID 485374 reaction equation
[H-].[Na+].[N:3]1([CH2:9][C:10]2[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:18][CH2:19][CH2:20][C:21]#[N:22]>CN(C)C=O>[N:3]1([CH2:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[O:16][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 214124-BromobutyronitrileHCID 24758Sodium hydrideHCID 8269741-(3-Hydroxybenzyl)piperidine

Product 1

HCID 197625514-{3-[(Piperidin-1-yl)methyl]phenoxy}butanenitrileYield 97.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of sodium hydride (1.5 g) and 3-(1-piperidinylmethyl)phenol (11.2 g) in dimethylformamide (60 ml) was stirred at room temperature for 5 h. 4-Bromobutannitrile (9.0 g) was added, and stirring was continued for a further 24 h. The mixture was poured onto ice and extracted with ethyl acetate which was washed with water and brine, and distilled to give the title compound as a colourless oil (14.78 g) b.p. 200°, 0.08 mm; tlc system A Rf 0.8.

Workup

  1. stirringstirring
  2. waitwas continued for a further 24 h
  3. additionThe mixture was poured onto ice
  4. extractionextracted with ethyl acetate which
  5. washwas washed with water and brine
  6. distillationdistilled

Sources & evidence

ORD record
ord-7c036b3ef5bd4220bc016a5c9a44bd45
Source dataset
uspto-grants-1985_08
Patent number
US04536508

Reaction notes

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