N-bromobutanimide → HCID 20087998, compound

HRID 275369Notes

Reaction equation

HRID 275369 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]([Cl:30])([Cl:29])[Cl:28])=[O:24])[CH2:19][CH2:18]3)[CH:9]=2)=[CH:4][CH:3]=1.[Br:31]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[Br:31][CH:21]1[CH2:22][CH:17]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:9]2)[CH2:18][CH2:19][N:20]1[C:23]([O:25][CH2:26][C:27]([Cl:28])([Cl:30])[Cl:29])=[O:24]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20087979HCID 20087979, compound

Product 1

HCID 20087998HCID 20087998, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2,2,2-trichloroethyl 4-[3-(4-fluorophenyl)-1H-indol-1-yl]piperidine-1-carboxylate 10b (4.0 g), N-bromosuccinimid (1.5 g) and tetrachloromethane (60 ml) was refluxed for 2 h. The reaction mixture was cooled to room temperature and the precipitate was filtered off. Evaporation of the solvent afforded the crude 2,2,2-trichloroethyl 2-bromo-4-[3-(4-fluorophenyl)-1H-indol-1-yl]piperidine-1-carboxylate (4.4 g) as an oil which was used without further purification. A mixture of the crude 2-bromo-indole (4.4 g), zinc powder (4.4 g) and 90% acetic acid in water (150 ml) was heated at 40° C. for 30 min. The reaction mixture was filtered and the solvent evaporated in vacuo. To the remaining oil was added ethyl acetate (50 ml) and the thus obtained solution was washed successively with water, 4N aqueous NaOH and brine. Evaporation of the solvents afforded the title compound as an oil (2.9 g).

Workup

  1. temperaturewas refluxed for 2 h
  2. filtrationthe precipitate was filtered off
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-200521dc373243ceb8c8d9d36eee169f
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

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