Propylamine → N-(1-propyl)-4-hydroxyphenoxyacetamide

HRID 1707998Notes

Reaction equation

HRID 1707998 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[OH:5][C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12](OC)=[O:13])=[CH:8][CH:7]=1>CO>[CH2:1]([NH:4][C:12](=[O:13])[CH2:11][O:10][C:9]1[CH:16]=[CH:17][C:6]([OH:5])=[CH:7][CH:8]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 602731Methyl 2-(4-hydroxyphenoxy)acetate

Product 1

HCID 15730023N-(1-propyl)-4-hydroxyphenoxyacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-propylamine (4.1 ml) and methyl 4-hydroxyphenoxyacetate (3.64 g) in methanol (50 ml) was left to stand for 72 hours at ambient temperature. The solvent was evaporated in vacuo and the residue taken up in ethyl acetate. The solution was washed sequentially with 1M HCl (2×25 ml) and brine (30 ml), then dried (MgSO4) and the solvent evaporated to give N-(1-propyl)-4-hydroxyphenoxyacetamide as a red oil, NMR: 0.95 (t, 3H, CH3), 1.55 (m, 2H, CH2) 3.3 (q 2H, CH2N), 4.4 (s, 2H, CH2O) 6.5-6.7 (broad s, 1H, OH), 6.8 (s, 4H, phenyl-H); m/e 227 (M+NH4)+, 210 (M+H)+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. washThe solution was washed sequentially with 1M HCl (2×25 ml) and brine (30 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-c1cc964854e843ea99bb077eded31f81
Source dataset
uspto-grants-1994_10
Patent number
US05356894

Reaction notes

Loading…