4-Piperidinol, 1-methyl- → HCID 70578172, compound

HRID 127936Notes

Reaction equation

HRID 127936 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=1.[CH3:15][N:16]1[CH2:21][CH2:20][CH:19](O)[CH2:18][CH2:17]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8](=[CH:15][N:16]([CH3:21])[CH3:17])[CH2:9][C:10]([O:12][CH:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)=[O:11])=[O:7])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 660484-Piperidinol, 1-methyl-HCID 776043-(4-Chlorobenzoyl)propionic acid

Product 1

HCID 70578172HCID 70578172, compound

Procedure

35.1 g of 1-methyl-4-piperidyl 3-p-chlorobenzoyl-4-dimethylamino-3-butenoate [obtainable by esterification of 3-p-chlorobenzoyl-propionic acid with 1-methyl-piperidin-4-ol to produce 1-methyl-4-piperidyl 3-p-chloro-benzoylpropionate and subsequent reaction of the latter with dimethylformamide dimethyl acetal in the presence of acetic acid at 120°] and 12 g of phenylhydrazine are warmed for 4 hours at 100°. The reaction mixture is subjected to the customary working up (benzene/water) and 1-methyl-4-piperidyl 5-p-chlorophenyl-1-phenyl-pyrazol-4-yl-acetate is obtained; m.p. 90°-93°. Hydrochloride, m.p. 234°-235°.

Sources & evidence

ORD record
ord-bc495d78a8f44500bf7e95ff04582c0f
Source dataset
uspto-grants-1981_03
Patent number
US04258047

Reaction notes

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