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

HRID 127939Notes

Reaction equation

HRID 127939 reaction equation
C1(N=[C:8]=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12]C2)CCCCC1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:25][C:24]=2[CH2:34][C:35]([OH:37])=[O:36])=[CH:19][CH:18]=1.OC1CCN(C)CC1>C1COCC1>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:25][C:24]=2[CH2:34][C:35]([O:37][CH:14]2[CH2:15][CH2:10][N:9]([CH3:8])[CH2:12][CH2:13]2)=[O:36])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 660484-Piperidinol, 1-methyl-HCID 622583Pyrazole-4-acetic acid, 5-(p-chlorophenyl)-1-phenyl-

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2.27 g of dicyclohexylcarbodiimide in 10 ml of dry THF is added slowly, at 5°-10°, to a solution of 3.13 g of (5-p-chlorophenyl-1-phenyl-pyrazol-4-yl)-acetic acid in 25 ml of dry THF. The mixture is stirred for 15 minutes at 5°-10°, a solution of 1.23 g of 4-hydroxy-1-methylpiperidine in 10 ml of dry THF is then added at 5°-10°, the resulting mixture is stirred for 3 hours at 20° and subjected to the customary working up, and 1-methyl-4-piperidyl (5-p-chlorophenyl-1-phenylpyrazol-4-yl)-acetate is obtained; m.p. 90°-93°. Hydrochloride, m.p. 234°-236°.

Workup

  1. stirringthe resulting mixture is stirred for 3 hours at 20°

Sources & evidence

ORD record
ord-c1adee3bd58b419b9692e9eb8a3306b8
Source dataset
uspto-grants-1981_03
Patent number
US04258047

Reaction notes

Loading…