Hydrochloric Acid → HCID 20274349, compound

HRID 371166Notes

Reaction equation

[CH2:1]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH:6]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:26])([CH3:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][C:13]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:2]([CH3:4])[CH3:3].O.NN.[OH-].[K+].Cl>C(OCC)C.C(O)CO>[CH2:1]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:26])([CH3:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][C:13]=1[O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH:2]([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2.32 g (5 mmoles) of N-isobutyl-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidone, 10.2 ml hydrazine hydrate and 20 ml ethylene glycol is heated at 100° C. for one hour. The mixture is cooled to 60° C, and 4.05 g (72.3 mmoles) solid potassium hydroxide is added. After heating at 200° C. for two hours, the reaction mixture is cooled and added to 500 ml 1N hydrochloric acid and 300 ml ethyl ether. The ether layer is separated, washed with brine, sodium bicarbonate solution, dried over magnesium sulfate and the solvent evaporated at reduced pressure. The crude product is purified, if desired, by column chromatography on silica gel.

Workup

temperatureThe mixture is cooled to 60° C
temperatureAfter heating at 200° C. for two hours
temperaturethe reaction mixture is cooled
customThe ether layer is separated
washwashed with brine, sodium bicarbonate solution
dry with materialdried over magnesium sulfate
customthe solvent evaporated at reduced pressure
customThe crude product is purified

Sources & evidence

ORD record: ord-f9d1949934ec48ddb0ed3ca63235752b
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04529732

Reaction notes

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