Dimethyl Sulfoxide → 1-[5-(4-Chlorophenyl)pyridin-2-yl]-4-(propan-2-yl)piperazine

HRID 80867Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.CS(C)=O.[CH:19]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([CH3:21])[CH3:20]>O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:25]3[CH2:26][CH2:27][N:22]([CH:19]([CH3:21])[CH3:20])[CH2:23][CH2:24]3)=[N:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-5-(4-chlorophenyl)pyridine (500 mg, 2.23 mmol), DMSO (2.0 mL) and 1-isopropylpiperazine (3 mL, 23.4 mmol) was stirred and heated on a 100° C. oil-bath overnight. The reaction mixture was poured into water (75 mL), and the solid was isolated by filtration, washed with water and dried. The crude product was purified by column chromatography on silica gel (Kiselgel 60, mesh 0.040-0.63) eluting with a mixture of ethyl acetate and methanol (4:1). Collecting the proper fractions afforded 600 mg (85%) of 1-[5-(4-chlorophenyl)pyridin-2-yl]-4-isopropylpiperazine.

Workup

customthe solid was isolated by filtration
washwashed with water
customdried
customThe crude product was purified by column chromatography on silica gel (Kiselgel 60, mesh 0.040-0.63)
washeluting with a mixture of ethyl acetate and methanol (4:1)
customCollecting the proper fractions

Sources & evidence

ORD record: ord-aa31204f69794e3a9f0466e3bad627a1
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846677B2

Reaction notes

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