1-Phenethylpiperazine → HCID 131724415, compound

HRID 2085928Notes

Reaction equation

HRID 2085928 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[CH:7][NH:8]2)(O)=[O:2].[I-].ClC1C=CC=C[N+]=1C.[CH2:31]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(C(C)C)C(C)C)C>CN1CCCC1=O.CC(C)=O>[OH2:2].[ClH:20].[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[CH:12][C:4]=3[C:1]([N:42]3[CH2:43][CH2:44][N:39]([CH2:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:40][CH2:41]3)=[O:2])[NH:8][CH:7]=2)=[O:21])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 792141-PhenethylpiperazineHCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 11415338HCID 11415338, compound

Product 1

HCID 131724415HCID 131724415, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A solution of 4-carboxy-3-(4-chlorobenzoyl)indole and 2-chloro-1-methylpyridinium iodide in N-methylpyrrolidone (NMP) is treated with a solution of 4-phenethylpiperazine and ethyldiisopropylamine (EDIPA) in NMP and subsequently stirred at room temperature for 3 hours. The mixture is worked up in the customary manner and the crude product is obtained. This is dissolved in acetone and the hydrochloride is precipitated using aqueous hydrochloric acid. After drying, [3-(4-chlorobenzoyl)-1H-indol-4-yl]-4-phenethylpiperazin-1-ylmethanone, hydrochloride hydrate, m.p. 187.4°, is obtained.

Workup

  1. customthe crude product is obtained
  2. customthe hydrochloride is precipitated
  3. customAfter drying

Sources & evidence

ORD record
ord-0fef31793c8e467fbdb47b8b3533d223
Source dataset
uspto-grants-2004_04
Patent number
US06723725B1

Reaction notes

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