Toluene → HCID 131712929, compound

HRID 1163911Notes

Reaction equation

HRID 1163911 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[CH2:2][CH2:3][CH3:4].[CH3:17][N:18]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[CH:19]([CH3:22])C=O.[C:33]1(C)C=CC=CC=1>>[CH2:1]([N:5]1[CH:6]=[CH:7][C:8]2[C:9]([N:10]=[C:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:17]1)[CH2:2][CH2:3][CH3:4].[CH3:17][N:18]([CH2:19][CH2:22][C:33]1[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]=[CH:7][C:8]2[C:9]=1[N:10]=[C:11]1[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]1)[C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24]

Participants

5

Reactant 3

HCID 1140TolueneHCID 45582N-Butyl-1H-indole-3-ethanamineHCID 20513196HCID 20513196, compound

Product 2

HCID 131712929HCID 131712929, compoundHCID 131712930HCID 131712930, compound

Procedure

To a solution of 3.4 g of N-n-butyl-tryptamine in 50 ml of toluene are added 4.6 g of N-methyl-N-benzyloxycarbonyl-2-aminopropionaldehyde, and the mixture is refluxed for 15 hours. After the reaction, the mixture is condensed under reduced pressure. Then, the residue obtained is purified by silica gel chromatography. 3.9 g of 1,2,3,4-tetrahydro-1-(2-N-methyl-N-benzyloxycarbonylamino)ethyl)-2-n-butyl-β-carboline (cis isomer) and 1.32 g of 1,2,3,4-tetrahydro-1-(2-(N-methyl-N-benzyloxycarbonylamino)ethyl-2-n-butyl-β-carboline (trans isomer) are obtained, respectively.

Workup

  1. temperaturethe mixture is refluxed for 15 hours
  2. customAfter the reaction
  3. customcondensed under reduced pressure
  4. customThen, the residue obtained
  5. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-b3e85bcbf88e47baa43e6bc954019c97
Source dataset
uspto-grants-1983_01
Patent number
US04367230

Reaction notes

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