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

HRID 326564

Reaction equation

HRID 326564 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), 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-5ffffaf14c6b4c27bc5d867700f1db58
Source dataset
uspto-grants-1993_12
Patent number
US05270311

Linked notes

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