4-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amine → 5,5a,8,8a-Tetrahydro-3-[4-[4-(6-chloro-2-pyrazinyl)-1-piperazinyl]butyl]-1,5-methanocyclopent[d]azepine-2,4(1H,3H)-dione

HRID 621782Notes

Reaction equation

HRID 621782 reaction equation
[CH:1]12[CH2:8][CH:7]=[CH: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:9](=[O:11])[CH:4]4[CH2:3][CH:2]([CH:1]5[CH2:8][CH:7]=[CH:6][CH:5]54)[C:12]3=[O:13])[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 53699477Bicyclo[3.3.0]oct-6-ene-2,4-dicarboxylic anhydride

Product 1

HCID 143701665,5a,8,8a-Tetrahydro-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 2.1 g (12 mmoles) of bicyclo[3.3.0]oct-6-ene-2,4-dicarboxylic anhydride and 3.2 g (12 mmoles) of 1-(4-aminobutyl)-4-(6-chloro-2-pyrazinyl)piperazine following the procedure in Example 4. 620 mg of the hydrochloride salt was isolated as the hemihydrate, m.p. 222°-224° C., after two recrystallizations from isopropanol.

Sources & evidence

ORD record
ord-5fd8d84f1d2d498a840a10b1e167bcc0
Source dataset
uspto-grants-1989_04
Patent number
US04824999

Reaction notes

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