1-Butanol → N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}butyl]-4-cyclohexene-1,2-dicarboximide hydrochloride

HRID 745211

Reaction equation

HRID 745211 reaction equation
[C@@H:1]12[C:10](=[O:11])[O:9][C:7](=O)[C@@H:2]1[CH2:3][CH:4]=[CH:5][CH2:6]2.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[N:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:19][CH2:18]1.C(O)CCC.[ClH:34]>C(O)(C)C>[ClH:34].[N:24]1[CH:25]=[CH:26][CH:27]=[N:28][C:23]=1[N:20]1[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[C:10](=[O:11])[CH:1]3[CH2:6][CH:5]=[CH:4][CH2:3][CH:2]3[C:7]2=[O:9])[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 98495Tetrahydrophthalic anhydride, cis-HCID 128407054-(2-Pyrimidinyl)-1-piperazinebutanamine

Product 1

HCID 15592392N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}butyl]-4-cyclohexene-1,2-dicarboximide hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of cis-4-cyclohexene-1,2-dicarboxylic anhydride (633 mg; 4.25 mmol), 1-(4-aminobutyl)-4-(2-pyrimidinyl)piperazine (1 g; 4.25 mmol) and n-butanol (10 ml) was heated under reflux for 6 hours. The solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography to give an oily substance. The oily substance was treated with a mixture of 3% hydrogen chloride in isopropanol, and the precipitate was recrystallized from isopropanol to give N-[4-{4-(2-pyrimidinyl)-1-piperazinyl}butyl]-4-cyclohexene-1,2-dicarboximide hydrochloride. M.P., 177°-179° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel chromatography
  5. customto give an oily substance
  6. customthe precipitate was recrystallized from isopropanol

Sources & evidence

ORD record
ord-723547244d2f468b915a287955bdb5d9
Source dataset
uspto-grants-1986_07
Patent number
US04598078

Linked notes

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