4-(1h-indol-3-yl)butan-2-one → 4-(1H-Indol-3-yl)butan-2-amine

HRID 555334Notes

Reaction equation

HRID 555334 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12](=O)[CH3:13])=[CH:2]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+]>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH:12]([NH2:21])[CH3:13])=[CH:2]1

Participants

5

Reactant 3

HCID 2469184-(1h-indol-3-yl)butan-2-oneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 273024-(1H-Indol-3-yl)butan-2-amineYield 62.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(1H-indol-3-yl)-butan-2-one (1.0 g, 5.3 mmol) in methanol (20 mL is added ammonium acetate (4.45 g, 57.73 mmol) and sodium cyanoborohydride (0.37 g, 5.9 mmol) at room temperature. The resulting mixture is allowed to stir for 64 hours at the same temperature. The reaction mixture is quenched by addition of 1 N hydrochloric acid and adjusted to pH ˜2. The mixture is concentrated and extracted with dichloromethane (50 mL). Then the aqueous phase is adjusted to pH ˜12 using 4 N aqueous sodium hydroxide and extracted with dichloromethane (3×50 mL). The combined organic phases are dried with sodium sulfate and concentrated in vacuo. The resulting residue is subjected to flash column chromatography (5%-30% methanol in dichloromethane) to afford 3-(1H-indol-3-yl)-1-methyl-propylamine (622 mg, 62%) as an oil.

Workup

  1. customThe reaction mixture is quenched by addition of 1 N hydrochloric acid
  2. concentrationThe mixture is concentrated
  3. extractionextracted with dichloromethane (50 mL)
  4. extractionextracted with dichloromethane (3×50 mL)
  5. dry with materialThe combined organic phases are dried with sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfd9c4d05a3848148488b2290e0ced51
Source dataset
uspto-grants-2011_11
Patent number
US08053442B2

Reaction notes

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