Methylamine → [(1H-indol-4-yl)methyl](methyl)amine

HRID 475291Notes

Reaction equation

HRID 475291 reaction equation
[CH3:1][NH2:2].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([CH:12]=O)[C:6]=2[CH:5]=[CH:4]1.[BH4-].[Na+]>CO>[NH:3]1[C:11]2[C:6](=[C:7]([CH2:12][NH:2][CH3:1])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 333703Indole-4-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12513770[(1H-indol-4-yl)methyl](methyl)amineYield 54.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methanamine (536 mg, 17.24 mmol) in MeOH (10 mL) was added 1H-indole-4-carbaldehyde (500 mg, 3.45 mmol). The reaction mixture was stirred at RT for 14 h. The reaction was cooled in an ice bath and NaBH4 (130 mg, 3.45 mmol) was added in several portions. The reaction was stirred at 0° C. for 5 min then stirred at RT for 4 h. The solvent was removed under reduced pressure to afford 300 mg (54.5%) of (1H-indol-4-yl)-N-methylmethanamine (116) which was used in the next step without further purification: MS (ESI) m/z=161.3 [M+1]+.

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. stirringThe reaction was stirred at 0° C. for 5 min
  3. stirringthen stirred at RT for 4 h
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cf5c22e753df4666b0d8b1bf5d330718
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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