Benzoyl chloride → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

HRID 609727

Reaction equation

HRID 609727 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[NH3:16].[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:15]=[C:14]2[CH2:20][CH2:21][N:22]([CH3:23])[CH3:24]

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 3602525-Bromo-N,N-Dimethyltryptamine

Product 2

HCID 222AmmoniaYield 3%HCID 196004435-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindoleYield 167.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Benzoyl chloride (1.7 mL, 14.6 mmol) was added to a solution of 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (Example 3a, 9.5 mmol) in dichloromethane (70 mL) containing triethylamine (4 mL, 28.7 mmol) and DMAP (206 mg, 1.7 mmol). The resulting solution was stirred at room temperature for 20 h. Dilution with dichloromethane (500 mL) was followed by sequential washing with water (200 mL) and brine (150 mL), drying over sodium sulfate and removal of the solvent in vacuo. Flash chromatography (silica gel, 3-5% 2M methanolic ammonia in dichloromethane) yielded 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (2.95 g, 84%).

Workup

  1. washby sequential washing with water (200 mL) and brine (150 mL)
  2. dry with materialdrying over sodium sulfate and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-7797e7fb49944762b4a1c1951ca1d748
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Linked notes

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