Potassium Hydroxide → 1-Benzyl-4-hydroxy-piperidine-4-carboxylic acid methyl-(4-trifluoromethoxy-phenyl)-amide

HRID 1949075Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([O:29]C(=O)C)([C:14](=[O:28])[N:15]([CH3:27])[C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>OS([O-])(=O)=O.[K+]>[CH3:27][N:15]([C:16]1[CH:17]=[CH:18][C:19]([O:22][C:23]([F:26])([F:24])[F:25])=[CH:20][CH:21]=1)[C:14]([C:11]1([OH:29])[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1)=[O:28]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 0.782 g (1.7 mmol) acetic acid 1-benzyl-4-[methyl-(4-trifluoromethoxy-phenyl)-carbamoyl]-piperidin-4-yl ester and excess KOH 5M was heated to 70° C. The mixture was diluted with KHSO4 1N aq. and extracted with ethyl acetate. the combined organic fractions were dried with MgSO4 and evaporated. The residue was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and HCOOH. The product containing fractions were evaporated to yield 0.41 g (58%) of the title compound. MS (m/e): 409.1 [(M+H)+].

Workup

extractionextracted with ethyl acetate
dry with materialthe combined organic fractions were dried with MgSO4
customevaporated
customThe residue was purified by preparative HPLC on reversed phase
washeluting with a gradient
customformed from acetonitrile, water and HCOOH
additionThe product containing fractions
customwere evaporated

Sources & evidence

ORD record: ord-f4b901d5562748b393dd6ee6125e385d
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399676B2

Reaction notes

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