Water → HCID 13180293, compound

HRID 867020Notes

Reaction equation

HRID 867020 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.Cl.[F:14][C:15]1[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=1[C:17]([CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:14][C:15]1[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=1[C:17]([CH:19]1[CH2:24][CH2:23][N:22]([CH2:2][CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)[CH2:21][CH2:20]1)=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 769243-(2-Bromoethyl)indoleHCID 13180313(2-Fluorophenyl)(piperidin-4-yl)methanone--hydrogen chloride (1/1)

Product 1

HCID 13180293HCID 13180293, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 9.1 g of 3-(2-bromoethyl)indole in 100 ml of dimethylformamide is added to a stirring solution of 11.2 g of 4-(2-fluorobenzoyl)piperidine hydrochloride and 13 g of potassium carbonate in 400 ml of dimethylformamide. The reaction mixture is stirred at ambient temperature for 24 hours, and then 800 ml of water are added dropwise, yielding a dark precipitate. This mixture is again stirred at ambient temperature for 24 hours and filtered to give a yellow crystalline material which is recrystallized thrice from an ethanol-water mixture to give an off-white crystalline material, mp 106°-108° C., 3-{2-[4-(2-fluorobenzoyl)piperidyl]ethyl}indole.

Workup

  1. customyielding a dark precipitate
  2. stirringThis mixture is again stirred at ambient temperature for 24 hours
  3. filtrationfiltered
  4. customto give a yellow crystalline material which
  5. customis recrystallized thrice from an ethanol-water mixture

Sources & evidence

ORD record
ord-b6c0a5dbd2ad4684997f52e42242eca0
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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