Potassium Fluoride → HCID 19040910, compound
Reaction equation
Cl.[F:2][C:3]([F:31])([F:30])[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)([OH:18])[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1.[CH2:32]([O:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42]Cl)=[CH:38][CH:37]=1)[C:33]#[CH:34].[F-].[K+]>>[CH2:32]([O:35][C:36]1[CH:37]=[CH:38][C:39]([CH2:42][N:15]2[CH2:16][CH2:17][CH:12]([C:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][C:3]([F:30])([F:2])[F:31])=[CH:10][CH:9]=3)([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:27])[F:28])=[CH:21][CH:20]=3)[OH:18])[CH2:13][CH2:14]2)=[CH:40][CH:41]=1)[C:33]#[CH:34]Participants
4
Procedure
A stirred mixture of 0.8 gram (0,0016 mole) of 4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine hydrochloride, 0.3 gram (0.0016 mole) of 4-(2-propyn-1-yloxy)phenylmethyl chloride and 0.5 gram (0.0079 mole) of potassium fluoride on Celite® filter aid in 50 mL of acetonitrile was heated at reflux for about 1.3 hours. After this time 0.5 mL (excess) of triethylamine was added, and the reaction mixture became homogeneous. Upon completion of addition, the reaction mixture was heated at reflux for an additional 18 hours. After this time the reaction mixture was cooled, filtered, and the filtrate concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with mixtures of 10-70% diethyl ether in hexane as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.6 gram of N-[4-(2-propyn-1-yloxy)phenylmethyl]-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.