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

HRID 915218Notes

Reaction equation

HRID 915218 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-f99d5ad2b7d14b348d03979b1b694811
Source dataset
uspto-grants-2007_09
Patent number
US07265132B2

Reaction notes

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