Tryptamine → N-[2-(1H-Indol-3-yl)-ethyl]-3,5-bis-trifluoromethyl-benzamide

HRID 1432447Notes

Reaction equation

HRID 1432447 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][NH2:12])=[CH:2]1.CCN(CC)CC.[F:20][C:21]([F:36])([F:35])[C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:25](Cl)=[O:26]>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][C:25](=[O:26])[C:24]2[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=[C:22]([C:21]([F:20])([F:35])[F:36])[CH:23]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 1150TryptamineHCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chloride

Product 1

HCID 22574444N-[2-(1H-Indol-3-yl)-ethyl]-3,5-bis-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1H-indol-3-yl)-ethylamine (1.0 g) in CH2Cl2 was added at 22° C. NEt3 (1.74 ml) and 3,5-bis-trifluoromethyl-benzoyl chloride (1.24 ml) and stirring was continued at 22° C. for 16 h. The mixture was washed with aqueous NaHCO3 and brine and the organic layer was dried and evaporated to give the title compound as a brown solid. MS: 401.3 ([M+H]+).

Workup

  1. washThe mixture was washed with aqueous NaHCO3 and brine
  2. customthe organic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-11d91979851b4354a25fcc39a8ad8be2
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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