Hydrochloric Acid → 1-[(4-Hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid

HRID 1642816Notes

Reaction equation

[F:1][C:2]([F:30])([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][N:14]([C:16]([N:18]3[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]3)=[O:17])[CH2:13][CH:12]([C:25]([O:27]C)=[O:26])[CH2:11]2)=[CH:6][CH:5]=1.CC(C)([O-])C.[K+].Cl>CO.O>[OH:24][CH:21]1[CH2:20][CH2:19][N:18]([C:16]([N:14]2[CH2:15][CH:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:29])[F:30])=[CH:5][CH:6]=3)[CH2:11][CH:12]([C:25]([OH:27])=[O:26])[CH2:13]2)=[O:17])[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 60 °C

Procedure

828 mg (1.92 mmol) of methyl 5-(4-(trifluoromethoxy)phenyl)-1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylate were dissolved in 70 ml of methanol, 2159 mg (19.24 mmol) of potassium tert-butoxide were added and the mixture was stirred at 60° C. overnight. For work-up, the reaction solution was diluted with water and acidified with 1N hydrochloric acid (pH 1). The mixture was extracted with ethyl acetate. The combined organic phases were dried with sodium sulphate and concentrated under reduced pressure. Yield: 749 mg (94% of theory)

Workup

extractionThe mixture was extracted with ethyl acetate
dry with materialThe combined organic phases were dried with sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6158678067ab4f039e354bc754a1fa97
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119663B2

Reaction notes

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