Pyrazole → 1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-pyrazole

HRID 483874

Reaction equation

[Br-].[N:2]1[CH:7]=[CH:6][CH:5]=[N:4][C:3]=1[N:8]1[CH2:17][CH2:16][N+:11]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:10][CH2:9]1.[NH:18]1[CH:22]=[CH:21][CH:20]=[N:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:4]1[CH:5]=[CH:6][CH:7]=[N:2][C:3]=1[N:8]1[CH2:9][CH2:10][N:11]([CH2:15][CH2:14][CH2:13][CH2:12][N:18]2[CH:22]=[CH:21][CH:20]=[N:19]2)[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 730 g (3.59 moles) of 8-(2-pyrimidinyl)-8-aza-5-azoniaspiro[4,5]decane bromide, 275 g (4.05 moles) of pyrazole and 745 g (5.4 moles) of potassium carbonate in 3 1 of dimethylformamide is heated to 140° C. for 14 hours. The mixture is evaporated under vacuum, chloroform is added, the solution is washed with water, dried over sodium sulfate and evaporated under vacuum, and 650 g (94%) of 1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-pyrazole are obtained in liquid form.

Workup

customThe mixture is evaporated under vacuum, chloroform
additionis added
washthe solution is washed with water
dry with materialdried over sodium sulfate
customevaporated under vacuum, and 650 g (94%) of 1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-pyrazole
customare obtained in liquid form

Sources & evidence

ORD record: ord-00438c32cf89405f95ce1ee33dcba21e
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05227486

Linked notes

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