Benzoyl chloride → Ethyl 1-benzoyl-4-[2-(1H-indol-3-yl)-ethyl]-3-oxo-2-piperazine-acetate

HRID 476875Notes

Reaction equation

HRID 476875 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][N:12]2[CH2:17][CH2:16][NH:15][CH:14]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]2=[O:24])=[CH:2]1.C(N(CC)CC)C.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[C:32]([N:15]1[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[C:13](=[O:24])[CH:14]1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14257258Ethyl 4-[2-(1H-indol-3-yl)-ethyl]-3-oxo-2-piperazine acetate

Product 1

HCID 14257259Ethyl 1-benzoyl-4-[2-(1H-indol-3-yl)-ethyl]-3-oxo-2-piperazine-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

22.4 g of the product of Step C were dissolved in 225 ml of tetrahydrofuran and 14.3 ml of triethylamine and the mixture was cooled to 5° C. 7.9 ml of benzoyl chloride were slowly added and then stirring was maintained for 1 hour at ambient temperature. The insoluble part was separated and the filtrate was evaporated to dryness to obtain 28.4 g of the expected product melting at 144° C.

Workup

  1. customThe insoluble part was separated
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-cd58bd7922ec4792be8b550e492bf76c
Source dataset
uspto-grants-1989_12
Patent number
US04886802

Reaction notes

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