Thionyl Chloride → {4-[2-(4-Fluoro-phenyl)ethyl]piperazin-1-yl}isoquinolin-3-ylmethanone

HRID 2054697Notes

Reaction equation

HRID 2054697 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=O)[N:2]=1.S(Cl)(Cl)=O.C1C2C(=CC=CC=2)C=C(C(Cl)=O)N=1.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:34][CH:33]=1>>[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][N:40]2[CH2:41][CH2:42][N:43]([C:11]([C:3]3[N:2]=[CH:1][C:10]4[C:5]([CH:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)=[O:13])[CH2:44][CH2:45]2)=[CH:34][CH:33]=1

Participants

5

Reactant 4

HCID 24386Thionyl ChlorideHCID 124656Isoquinoline-3-carboxylic acidHCID 112545221-(2-(4-Fluorophenyl)ethyl)piperazineHCID 22064853Isoquinoline-3-carbonyl chloride

Product 1

HCID 44215581{4-[2-(4-Fluoro-phenyl)ethyl]piperazin-1-yl}isoquinolin-3-ylmethanone

Procedure

Analogously to Example 3, firstly isoquinoline-3-carboxylic acid is reacted with thionyl chloride, and the resultant isoquinoline-3-carbonyl chloride is reacted with 1-[2-(4-fluorophenyl)ethyl]piperazine, giving {4-[2-(4-fluoro-phenyl)ethyl]piperazin-1-yl}isoquinolin-3-ylmethanone.

Sources & evidence

ORD record
ord-12574c840ca043dda608e9a7b995a546
Source dataset
uspto-grants-2008_02
Patent number
US07329749B2

Reaction notes

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