Methylamine → 2-[1-(Methylamino)ethyl]aniline
Reaction equation
[CH3:1][NH2:2].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=O)[CH3:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCl.O>[CH3:1][NH:2][CH:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:3])[CH3:11]Participants
7
Conditions
- Temperature
- 5 °C
Procedure
Acetic acid (10 drops) was added to a solution of methylamine (10 g) in dichloromethane (150 ml) cooled to 5° C., followed by o-aminoacetophenone (3.5 g, 25.9 mmol), and the solution stirred for 10 minutes. Sodium triacetoxyborohydride (1.5 g, 38.8 mmol) was added and the reaction stirred at room temperature for 72 hours. The reaction was diluted with water, the layers separated, and the organic solution evaporated under reduced pressure to give the title compound as a yellow oil.
Workup
- stirringthe reaction stirred at room temperature for 72 hours
- customthe layers separated
- customthe organic solution evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-1b9fbd37556e4fefb36d83e1ba61656c
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07442795B2
Reaction notes
Loading…