Hydrochloric Acid → 1-(8-Aza-bicyclo[3.2.1]oct-8-yl)-4-[4-(1H-indol-4-yl)-piperazin-1-yl]-2-phenyl-butan-1-one

HRID 975815Notes

Reaction equation

HRID 975815 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([N:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH:16]12[N:23]([C:24](=[O:35])[CH:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:26][CH2:27]Cl)[CH:20]([CH2:21][CH2:22]1)[CH2:19][CH2:18][CH2:17]2.C(N(C(C)C)CC)(C)C.[I-].[K+].Cl>CN(C)C=O>[CH:20]12[N:23]([C:24](=[O:35])[CH:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:26][CH2:27][N:13]3[CH2:14][CH2:15][N:10]([C:5]4[CH:6]=[CH:7][CH:8]=[C:9]5[C:4]=4[CH:3]=[CH:2][NH:1]5)[CH2:11][CH2:12]3)[CH:16]([CH2:22][CH2:21]1)[CH2:17][CH2:18][CH2:19]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 199683601-(8-Aza-bicyclo[3.2.1]oct-8-yl)-4-chloro-2-phenyl-butan-1-one

Product 1

HCID 199683641-(8-Aza-bicyclo[3.2.1]oct-8-yl)-4-[4-(1H-indol-4-yl)-piperazin-1-yl]-2-phenyl-butan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 4-(1H-indol-4-yl)-piperazine (1.0 g, 4.97 mmole), 1-(8-aza-bicyclo[3.2.1]oct-8-yl)-4-chloro-2-phenyl-butan-1-one (1.6 g, 4.97 mmole), diisopropylethylamine (0.65 g, 4.97 mmole) and potassium iodide (0.83 g, 4.97 mmole) in dimethylformamide (8 mL) in the manner described in example 2 to yield 0.6 g of product as the hydrochloride 0.75 hydrate, m.p. 150°-170° C.

Sources & evidence

ORD record
ord-3a211349bf5543509552ecfe9890c20e
Source dataset
uspto-grants-1997_03
Patent number
US05610154

Reaction notes

Loading…