1-Phenethylpiperazine → (1h-Indol-4-yl)-(4-phenethylpiperazin-1-yl)methanone, hydrochloride

HRID 6686

Reaction equation

HRID 6686 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)([OH:3])=O.[I-].[Cl:14]C1C=CC=C[N+]=1C.[CH2:22]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)C(C)C)C>CN1CCCC1=O.CC(C)=O>[ClH:14].[NH:8]1[C:9]2[C:5](=[C:4]([C:1]([N:33]3[CH2:34][CH2:35][N:30]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:31][CH2:32]3)=[O:3])[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7]1

Participants

7

Reactant 4

HCID 792141-PhenethylpiperazineHCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 595229Indole-4-carboxylic acid

Product 1

HCID 131725875(1h-Indol-4-yl)-(4-phenethylpiperazin-1-yl)methanone, hydrochlorideYield 100.1%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 2.0 g of 4-carboxyindole and 8.1 g of 2-chloro-1-methylpyridinium iodide in 60 ml of N-methylpyrrolidone (NMP) is treated with a solution of 2.36 g of 4-phenethylpiperazine and 8.2 g of ethyldi-isopropylamine (EDIPA) in 20 ml of 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, 4.59 g of (1H-indol-4-yl)-(4-phenethylpiperazin-1-yl)methanone, hydrochloride, m.p. 289.3°, is obtained.

Workup

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

Sources & evidence

ORD record
ord-d902f388819647f19c93534fd4a3ba09
Source dataset
uspto-grants-2006_08
Patent number
US07084143B2

Linked notes

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