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

HRID 326559

Reaction equation

HRID 326559 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. customdried (MGSO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-b68eb538d76a4b6b90924eb19a1c9e97
Source dataset
uspto-grants-1993_12
Patent number
US05270311

Linked notes

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