Dimethylformamide → HCID 19789768, compound

HRID 1656109Notes

Reaction equation

HRID 1656109 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27]N(C=O)C.[H-].[Na+].CI>O>[CH3:27][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:12]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 455841H-Indole-3-ethanamine, N,N-bis(phenylmethyl)-

Product 1

HCID 19789768HCID 19789768, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,N-dibenzyl-tryptamine (1.72 g) was added to an anhydrous DMF solution containing 0.24 g of NaH (60% nujol) and the mixture was stirred for 15 minutes. Methyl iodide (0.31 ml) was added and the mixture was stirred for one hour. Water was added and the solvent was evaporated off. The residue to which water was added was extracted with IPE, the extract was washed with water and the brine and dried over magnesium sulfate. The crude product was purified by column chromatography on silica gel. Eluates with ethyl acetate/hexane (1/9) afforded 1.58 g of the oily title compound.

Workup

  1. stirringthe mixture was stirred for one hour
  2. customthe solvent was evaporated off
  3. additionThe residue to which water was added
  4. extractionwas extracted with IPE
  5. washthe extract was washed with water
  6. dry with materialthe brine and dried over magnesium sulfate
  7. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3fccf66aec00466b8c6ae87a2e04ca95
Source dataset
uspto-grants-1993_10
Patent number
US05252580

Reaction notes

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