Water → (1,3-dimethyl-1H-indol-2-yl)-N-methylmethanamine

HRID 1362440Notes

Reaction equation

HRID 1362440 reaction equation
[CH3:1][NH2:2].[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH3:13])=[C:5]1[CH:14]=O.[BH4-].[Na+].O>CO>[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH3:13])=[C:5]1[CH2:14][NH:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 27714681,3-dimethyl-1H-indole-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 22139131(1,3-dimethyl-1H-indol-2-yl)-N-methylmethanamineYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Methylamine (0.53 mL, 13.1 mmol) was added to a solution of 1,3-dimethyl-1H indole-2-carbaldehyde (760 mg, 4.3 mmol) in methanol (15 mL) and stirred for 5 h. The mixture was cooled to 0° C. and sodium borohydride (159 mg, 4.3 mmol) added slowly. The mixture was warmed to rt and stirred overnight. Water (3 mL) was added slowly at 0° C. and evaporated to a paste. Water was added and the mixture extracted with dichloromethane. The organic phase was washed with water, dried and evaporated to afford the title compound (690 mg, 85%). 1H NMR (400 MHz, DMSO-d6) δ 7.44 (d, J=7.8 Hz, 1H), 7.34 (d, J=8.1 Hz, 1H), 7.10 (t, J=7.6 Hz, 1H), 6.98 (t, J=8.0 Hz, 1H), 3.77 (s, 2H), 3.71 (s, 3H), 2.27 (s, 3H), 2.23 (s, 3H).

Workup

  1. temperatureThe mixture was warmed to rt
  2. stirringstirred overnight
  3. customevaporated to a paste
  4. additionWater was added
  5. extractionthe mixture extracted with dichloromethane
  6. washThe organic phase was washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-70f793f84e19442f9d15b4e71c43a06d
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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