4-Toluenesulfonyl chloride → HCID 19789761, compound

HRID 1656108Notes

Reaction equation

HRID 1656108 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.[OH-].[Na+].[S:29](Cl)([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[S:29]([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)([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 455841H-Indole-3-ethanamine, N,N-bis(phenylmethyl)-

Product 1

HCID 19789761HCID 19789761, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent

Procedure

N,N-dibenzyl-tryptamine (1.70 g) and tetra-n-butyl ammonium hydrogensulfate (0.17 g) in benzene (5 ml) were added to 50% aqueous NaOH solution (5 ml) and tosyl chloride (1.43 g) and the mixture was stirred at room temperature for 2 hrs. The organic layer was separated, washed with water and then brine and dried over magnesium sulfate. The solvent was evaporated off. Crystallization from acetone/hexane afforded 1.83 g of the title compound.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialbrine and dried over magnesium sulfate
  4. customThe solvent was evaporated off
  5. customCrystallization from acetone/hexane

Sources & evidence

ORD record
ord-f59b0b7a0559472cbfb280cded0e6410
Source dataset
uspto-grants-1993_10
Patent number
US05252580

Reaction notes

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