Benzyltrimethylammonium hydroxide → HCID 13790605, compound

HRID 485381Notes

Reaction equation

HRID 485381 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.[OH-].[CH2:16]([N+:23](C)(C)C)[C:17]1C=CC=C[CH:18]=1>C(#N)C=C>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[O:14][CH2:18][CH2:17][C:16]#[N:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 66854Benzyltrimethylammonium hydroxideHCID 8269741-(3-Hydroxybenzyl)piperidine

Product 1

HCID 13790605HCID 13790605, compound

Reagents, catalysts & solvents 1

HCID 7855AcrylonitrileSolvent

Procedure

A solution of 3-(1-piperidinylmethyl)phenol (26 g), acrylonitrile (100 ml) and benzyltrimethylammonium hydroxide (40% methanolic solution, 5 ml) was heated at reflux for 40 h. The mixture was evaporated in vacuo, diluted with ether (300 ml) and filtered. The filtrate was washed with 2N sodium hydroxide, water and distilled to give the title compound as a colourless oil (17.5 g) b.p. 170°, 0.07 mm; tlc system B, Rf 0.8.

Workup

  1. temperatureat reflux for 40 h
  2. customThe mixture was evaporated in vacuo
  3. additiondiluted with ether (300 ml)
  4. filtrationfiltered
  5. washThe filtrate was washed with 2N sodium hydroxide, water
  6. distillationdistilled

Sources & evidence

ORD record
ord-bf150c6390af496e9622e0b44c30a90a
Source dataset
uspto-grants-1985_08
Patent number
US04536508

Reaction notes

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