4-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amine → Hexahydro-3-[4-[4-(6-chloro-2-pyrazinyl)-1-piperazinyl]butyl]-1,5-methanocyclopent[d]azepine-2,4(1H,3H)-dione

HRID 621780Notes

Reaction equation

HRID 621780 reaction equation
[CH:1]12[CH2:8][CH2:7][CH2:6][CH:5]1[CH:4]1[C:9]([O:11][C:12](=[O:13])[CH:2]2[CH2:3]1)=O.[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[N:29][CH:28]=[C:27]([Cl:31])[N:26]=2)[CH2:21][CH2:20]1>>[Cl:31][C:27]1[N:26]=[C:25]([N:22]2[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][CH2:15][N:14]3[C:12](=[O:13])[CH:2]4[CH2:3][CH:4]([CH:5]5[CH2:6][CH2:7][CH2:8][CH:1]54)[C:9]3=[O:11])[CH2:24][CH2:23]2)[CH:30]=[N:29][CH:28]=1

Participants

3

Reactant 2

HCID 140865264-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amineHCID 53869218Bicyclo[3.3.0]-octane-2,4-dicarboxylic anhydride

Product 1

HCID 14370160Hexahydro-3-[4-[4-(6-chloro-2-pyrazinyl)-1-piperazinyl]butyl]-1,5-methanocyclopent[d]azepine-2,4(1H,3H)-dione

Procedure

The title compound was prepared from 4.58 g (25.4 mmoles) of bicyclo[3.3.0]-octane-2,4-dicarboxylic anhydride and 7.10 g (26 mmoles) of 1-(4-aminobutyl)-4-(6-chloro-2-pyrazinyl)-piperazine following the procedure in Example 1. 7.24 g of the hydrochloride salt was isolated as the one-quarter hydrate, m.p. 223°-225° C.

Sources & evidence

ORD record
ord-06151931f9d048ed8d5a896b5d2dc735
Source dataset
uspto-grants-1989_04
Patent number
US04824999

Reaction notes

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