Hydrochloric Acid → N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}butyl]cyclohexane-1,2-dicarboximide hydrochloride

HRID 745213Notes

Reaction equation

HRID 745213 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15](=[O:16])[CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]2[C:7]1=[O:8].[N:17]1[CH:22]=[CH:21][CH:20]=[N:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+].[ClH:35]>CN(C)C=O>[ClH:35].[N:17]1[CH:22]=[CH:21][CH:20]=[N:19][C:18]=1[N:23]1[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:15](=[O:16])[CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]3[C:7]2=[O:8])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 887471-(2-Pyrimidinyl)piperazineHCID 13671565N-(4-bromobutyl)cyclohexane-1,2-dicarboximide

Product 1

HCID 23315240N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}butyl]cyclohexane-1,2-dicarboximide hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-bromobutyl)cyclohexane-1,2-dicarboximide (10.00 g), 1-(2-pyrimidyl)piperazine (4.75 g), anhydrous potassium carbonate powder (8.00 g) and anhydrous dimethylformamide (100 ml) was stirred at 100°-110° C. for 9 hours. The solvent was removed from the reaction mixture under reduced pressure, and the residue was purified by chromatography to give an oily substance, which was then treated with hydrogen chloride to give N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}butyl]cyclohexane-1,2-dicarboximide hydrochloride. M.P., 168°-169° C.

Workup

  1. customThe solvent was removed from the reaction mixture under reduced pressure
  2. customthe residue was purified by chromatography
  3. customto give an oily substance, which

Sources & evidence

ORD record
ord-6b35f752576b44fe9eb2069991caa63c
Source dataset
uspto-grants-1986_07
Patent number
US04598078

Reaction notes

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