Potassium Carbonate → 2-(4-((4-(4-Aminophenyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

HRID 515337Notes

Reaction equation

Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:12][C:11]1[CH:13]=[CH:14][C:8]([CH:5]2[CH2:6][CH2:7][N:2]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([OH:32])([C:24]([F:25])([F:26])[F:27])[C:28]([F:29])([F:30])[F:31])=[CH:21][CH:22]=3)[CH2:3][CH2:4]2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-(piperidin-4-yl)aniline hydrochloride (14.10 mmol, 3 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (14.10 mmol, 4.75 g) and potassium carbonate (42.3 mmol, 5.85 g) in acetonitrile was heated to 60° C. (heating block temperature) for 20 hours. The reaction was concentrated under reduced pressure and dichloromethane was added. The mixture was chromatographed on silica (eluting with a gradient of dichloromethane to ethyl acetate) to give the title compound (770 mg). MS (ESI) m/z 433.3 [M+H]+

Workup

temperature(heating block temperature) for 20 hours
concentrationThe reaction was concentrated under reduced pressure and dichloromethane
additionwas added
customThe mixture was chromatographed on silica (
washeluting with a gradient of dichloromethane to ethyl acetate)

Sources & evidence

ORD record: ord-6d6f8ab3d01142cea90cb3edd0a8d930
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108939B2

Reaction notes

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