Water → (7-Ethyl-3-methyl-1h-indol-2-yl)-n-methanamine

HRID 1362446Notes

Reaction equation

HRID 1362446 reaction equation
C[NH2:2].[CH2:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([CH:14]=O)=[C:10]2[CH3:16])[CH3:4].[BH4-].[Na+].O>CO>[CH3:4][CH2:3][C:5]1[C:13]2[NH:12][C:11]([CH2:14][NH2:2])=[C:10]([CH3:16])[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 592775647-ethyl-3-methyl-1H-indole-2-carbaldehyde

Product 1

HCID 66967213(7-Ethyl-3-methyl-1h-indol-2-yl)-n-methanamineYield 75.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Methylamine (0.7 mL, 17.6 mmol) was added to a solution of 7-ethyl-3-methyl-1H-indole-2-carbaldehyde (1.1 mg, 5.8 mmol) in methanol (5 mL) and stirred for 5 h. The mixture was cooled to 0° C. and sodium borohydride (218 mg, 5.8 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 (826 mg, 75%). 1H NMR (400 MHz, CDCl3) δ 8.22 (s, 1H), 7.34 (d, J=7.7 Hz, 1H), 7.01 (t, J=7.6 Hz, 1H), 6.96 (d, J=6.8 Hz, 1H), 3.87 (s, 2H), 2.79 (q, J=7.5 Hz, 2H), 2.45 (s, 3H), 2.24 (s, 3H), 1.31 (t, J=7.6 Hz, 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-bd7c56b71b6948728a3eb68fe270bda5
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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