Dimethylamine → 2-(3-aminooxetan-3-yl)-N,N-dimethylacetamide

HRID 1480151Notes

Reaction equation

HRID 1480151 reaction equation
[NH2:1][C:2]1([CH2:6][C:7]([O:9]CC)=O)[CH2:5][O:4][CH2:3]1.[CH3:12][NH:13][CH3:14].O>C1(C)C=CC=CC=1>[NH2:1][C:2]1([CH2:6][C:7]([N:13]([CH3:14])[CH3:12])=[O:9])[CH2:5][O:4][CH2:3]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 55280628Ethyl 2-(3-aminooxetan-3-yl)acetate

Product 1

HCID 841076792-(3-aminooxetan-3-yl)-N,N-dimethylacetamideYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a microwave tube was added ethyl 2-(3-aminooxetan-3-yl)acetate (CAN 1207175-54-9, 470 mg, 2.95 mmol). Toluene (7.0 ml) and 40%-dimethylamine solution in water (8.9 g, 10.0 ml, 79.0 mmol) were added. The tube was sealed and the reaction mixture was stirred vigorously at room temperature for 7 days. The reaction mixture was concentrated in vacuo and azeotroped several times with 30 mL toluene. The crude solid was dried under high vacuum at 40° C. for 3 hours to yield the title compound (405 mg, 87%). MS (ESI, m/z): 159.1 (M+H+).

Workup

  1. customThe tube was sealed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customazeotroped several times with 30 mL toluene
  4. customThe crude solid was dried under high vacuum at 40° C. for 3 hours

Sources & evidence

ORD record
ord-8f901fbe04b04054bb00ab8a33fa53f0
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

Loading…