Potassium Iodide → 1-(8-Aza-bicyclo[3.2.1]oct-8-yl)-4-[4-(2-methoxy-5-trifluoromethyl-phenyl)-piperazin-1-yl]-2-phenyl-butan-1-one

HRID 975816Notes

Reaction equation

HRID 975816 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[CH:19]12[N:26]([C:27](=[O:38])[CH:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:29][CH2:30]Cl)[CH:23]([CH2:24][CH2:25]1)[CH2:22][CH2:21][CH2:20]2.C(N(C(C)C)CC)(C)C.[I-].[K+].O.Cl.Cl>CN(C)C=O>[CH:23]12[N:26]([C:27](=[O:38])[CH:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:29][CH2:30][N:16]3[CH2:15][CH2:14][N:13]([C:4]4[CH:5]=[C:6]([C:9]([F:10])([F:12])[F:11])[CH:7]=[CH:8][C:3]=4[O:2][CH3:1])[CH2:18][CH2:17]3)[CH:19]([CH2:25][CH2:24]1)[CH2:20][CH2:21][CH2:22]2

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 151247944-(2-Methoxy-5-trifluoromethyl-phenyl)-piperazineHCID 199683601-(8-Aza-bicyclo[3.2.1]oct-8-yl)-4-chloro-2-phenyl-butan-1-oneHCID 21226127Hydrate;dihydrochloride

Product 1

HCID 199683521-(8-Aza-bicyclo[3.2.1]oct-8-yl)-4-[4-(2-methoxy-5-trifluoromethyl-phenyl)-piperazin-1-yl]-2-phenyl-butan-1-oneYield 67.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 4-(2-methoxy-5-trifluoromethyl-phenyl)-piperazine 0.7 g, 2.3 mmole, prepared according to the method reported in example 2), 1-(8-aza-bicyclo[3.2.1]oct-8-yl)-4-chloro-2-phenyl-butan-1-one (0.7 g, 2.3 mmole), diisopropylethylamine (0.4 g, 3.0 mmole) and potassium iodide (0.5 g, 3.0 mmole) in dimethylformamide (25 mL) in the manner described in example 2 to yield 0.8 g of title product as the hydrochloride hemihydrate, m.p. 198°-199° C.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-b935bc3b175849baa31fb096d79f71fc
Source dataset
uspto-grants-1997_03
Patent number
US05610154

Reaction notes

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