Water → N-Methyl-1-(3-methyl-1H-indol-2-YL)methanamine

HRID 2097140Notes

Reaction equation

HRID 2097140 reaction equation
[CH3:1][NH2:2].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH:13]=O.[BH4-].[Na+].O>CO>[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH2:13][NH:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 2772603-Methyl-1H-indole-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 26722512N-Methyl-1-(3-methyl-1H-indol-2-YL)methanamineYield 71.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methylamine (0.34 mL, 8.4 mmol, 33% in ethanol) was added to a solution of 3-methylindole-2-carboxaldehyde (447 mg, 2.8 mmol) in methanol (10 mL) and stirred for 5 hours. Sodium borohydride (104 mg, 2.8 mmol) was slowly added at 0° C. The resultant mixture was warmed to room temperature and stirred overnight. Water (2 mL) was added slowly at 0° C. and the mixture was evaporated to a paste. The paste was partitioned between water (2 mL) and dichloromethane (15 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (2×15 mL). The combined organic phases were dried and evaporated to afford title compound (348 mg, 71%). NMR (400 MHz, DMSO-d6): 10.63 (s, 1H), 7.38 (d, J=7.7 Hz, 1H), 7.25 (d, J=8.0 Hz, 1H), 6.99 (t, J=8.0 Hz, 1H), 6.92 (t, J=6.6 Hz, 1H), 3.73 (s, 2H), 2.25 (s, 3H), 2.19 (s, 3H).

Workup

  1. stirringstirred overnight
  2. customthe mixture was evaporated to a paste
  3. customThe paste was partitioned between water (2 mL) and dichloromethane (15 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with dichloromethane (2×15 mL)
  6. customThe combined organic phases were dried
  7. customevaporated

Sources & evidence

ORD record
ord-83da030bc1bb4418a41abcd9219c2a83
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

Loading…