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

HRID 1179167Notes

Reaction equation

HRID 1179167 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-d38201059dd84405b5f30f5193a7e271
Source dataset
uspto-grants-2007_10
Patent number
US07279472B2

Reaction notes

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