Water → HCID 54133375, compound

HRID 1816749Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH3:2].[CH2:18]([O:21][CH:22]1[CH2:27][CH2:26][CH:25]([CH:28]2[CH2:33][CH2:32][CH:31](OS(C)(=O)=O)[CH2:30][CH2:29]2)[CH2:24][CH2:23]1)[CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][N:14]([CH:31]3[CH2:30][CH2:29][CH:28]([CH:25]4[CH2:24][CH2:23][CH:22]([O:21][CH2:18][CH2:19][CH3:20])[CH2:27][CH2:26]4)[CH2:33][CH2:32]3)[CH2:15][CH2:16]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-piperazinylbenzoic acid ethyl ester (1.03 g), 4′-propoxy-4-methylsulfonyloxy-1,1′-bicyclohexane (1.4 g), potassium carbonate (0.91 g) in N,N-dimethylformamide (10 ml) was stirred for 8 hours at 130° C. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure. The residue was chromatographed on a column of silica gel eluting with dichloromethane/methyl alcohol (200:1) to give 4-[4-(4′-propoxy-1,1′-bicyclohexan-4-yl)piperazin-1-yl]benzoic acid ethyl ester (0.26 g).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with brine
customdried
customthe solvent was evaporated under reduced pressure
customThe residue was chromatographed on a column of silica gel eluting with dichloromethane/methyl alcohol (200:1)

Sources & evidence

ORD record: ord-c0dc4ec1bf1b490e9e0d9d8676853aa8
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884868B1

Reaction notes

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