Acetic Acid → 1-Methyl-4-piperidyl (5-p-chlorophenyl-1-phenylpyrazol-4-yl)-acetate

HRID 127937Notes

Reaction equation

HRID 127937 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([CH2:8][CH2:9][C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[O:11])=O)=[CH:4][CH:3]=1.[CH3:22]OC(OC)N(C)C.C(O)(=O)C.[C:34]1([NH:40][NH2:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]2[N:40]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:41]=[CH:22][C:8]=2[CH2:9][C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7516PhenylhydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 234708451-Methyl-4-piperidyl 3-p-chloro-benzoylpropionate

Product 1

HCID 234708511-Methyl-4-piperidyl (5-p-chlorophenyl-1-phenylpyrazol-4-yl)-acetate

Reagents, catalysts & solvents 1

HCID 22272175Benzene--water (1/1)Solvent

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°.

Workup

  1. temperatureare warmed for 4 hours at 100°

Sources & evidence

ORD record
ord-4c6e8df6b6a3433093f1a5db930cc267
Source dataset
uspto-grants-1981_03
Patent number
US04258047

Reaction notes

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