Methylamine → 2-[1-(Methylamino)ethyl]aniline

HRID 1243564Notes

Reaction equation

HRID 1243564 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

Reactant 3

HCID 6329MethylamineHCID 110862'-AminoacetophenoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 219255892-[1-(Methylamino)ethyl]aniline

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

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

  1. stirringthe reaction stirred at room temperature for 72 hours
  2. customthe layers separated
  3. customthe organic solution evaporated under reduced pressure

Sources & evidence

ORD record
ord-5296d87e9d4943beb0f296c5c22a863c
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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