Tert-Butylamine → 3-(t-Butyl-amino)-N-methoxy-N-methyl-propanamide

HRID 1827817Notes

Reaction equation

HRID 1827817 reaction equation
[CH3:1][O:2][N:3]([CH3:8])[C:4](=[O:7])[CH:5]=[CH2:6].[C:9]([NH2:13])([CH3:12])([CH3:11])[CH3:10]>>[C:9]([NH:13][CH2:6][CH2:5][C:4]([N:3]([O:2][CH3:1])[CH3:8])=[O:7])([CH3:12])([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 294174N-methoxy-N-methylprop-2-enamide

Product 1

HCID 220634023-(t-Butyl-amino)-N-methoxy-N-methyl-propanamideYield 70%

Procedure

N-Methoxy-N-methyl-acrylamide (5 g, 43.4 mmol, 1.0 equiv) was dissolved in t-butylamine (3.36 g, 46 mmol, 1.06 equiv). The resulting solution was stirred at room temperature for 48 h. The excess primary amine was removed in vacuo and the crude product was purified by flash chromatography on silica using 100% CH2Cl2 to 2% MeOH in CH2Cl2 to give the desired product as a light yellow oil (5.7 g, 70%); MS, m/z 189=M+1.

Workup

  1. customThe excess primary amine was removed in vacuo
  2. customthe crude product was purified by flash chromatography on silica using 100% CH2Cl2 to 2% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-9488549a33b4453b97e8f5e04933f0ee
Source dataset
uspto-grants-2006_06
Patent number
US07056915B2

Reaction notes

Loading…