O-Xylene → 3-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-8,8-dimethyl-3-azabicyclo[3.2.1]octane-2,4-dione

HRID 1253270Notes

Reaction equation

HRID 1253270 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:6]2[C:7]([O:9][C:10](=[O:11])[CH:3]1[CH2:4][CH2:5]2)=O.[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[N:28][CH:27]=[C:26]([Cl:30])[N:25]=2)[CH2:20][CH2:19]1.C1(C)C(C)=CC=CC=1>O>[Cl:30][C:26]1[N:25]=[C:24]([N:21]2[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][CH2:15][CH2:14][N:13]3[C:7](=[O:9])[CH:6]4[C:2]([CH3:1])([CH3:12])[CH:3]([CH2:4][CH2:5]4)[C:10]3=[O:11])[CH2:23][CH2:22]2)[CH:29]=[N:28][CH:27]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 140865264-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amineHCID 197972038,8-Dimethyl-3-oxabicyclo(3.2.1)octane-2,4-dione

Product 1

HCID 141563833-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-8,8-dimethyl-3-azabicyclo[3.2.1]octane-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,2-Dimethylcyclopentane-1,3-dicarboxylic anhydride (1.68 g., 10 mmole) and 1-(4-aminobutyl)-4-(6-chloro-2-pyrazinyl)piperazine (2.97 g., 11 mmole) were combined in 500 ml. of xylene and refluxed for 48 hours with Dean-Stark water removal. Concentration in vacuum, column chromatography on 100 g. of silica gel with chloroform, and recrystallization from 50 ml. of isopropanol with addition of 4N isopropanolic HCl gave 0.55 g. of the title compound as the monohydrochloride; m.p. 210° C. (d).

Workup

  1. concentrationConcentration in vacuum, column chromatography on 100 g
  2. customof silica gel with chloroform, and recrystallization from 50 ml
  3. additionof isopropanol with addition of 4N isopropanolic HCl
  4. customgave 0.55 g

Sources & evidence

ORD record
ord-759e9be378344115804eb0877f7c45f7
Source dataset
uspto-grants-1988_05
Patent number
US04748240

Reaction notes

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