Potassium Carbonate → 4-(3-(Trifluoromethyl)phenyl)-3-hydroxy-1-(4-phenyl-3-butynyl)piperidine

HRID 366512Notes

Reaction equation

HRID 366512 reaction equation
S([CH2:5][CH2:6][C:7]#[C:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(=O)=O.Cl.[F:16][C:17]([F:32])([F:31])[C:18]1[CH:19]=[C:20]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH:25]2[OH:30])[CH:21]=[CH:22][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[F:32][C:17]([F:16])([F:31])[C:18]1[CH:19]=[C:20]([CH:24]2[CH2:29][CH2:28][N:27]([CH2:5][CH2:6][C:7]#[C:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:26][CH:25]2[OH:30])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 184279454-(3-(Trifluoromethyl)phenyl)piperidin-3-ol hydrochlorideHCID 184279661-Mesyl-4-phenylbut-3-yne

Product 1

HCID 184279704-(3-(Trifluoromethyl)phenyl)-3-hydroxy-1-(4-phenyl-3-butynyl)piperidineYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-mesyl-4-phenylbut-3-yne (352 mg, 1.57 mmol), 4-(3-(trifluoromethyl)phenyl)piperidin-3-ol hydrochloride (530 mg, 1.88 mmol) and K2CO3 (542 mg, 3.93 mmol) in 20 mL of CH3CN is refluxed for 12 hr. The mixture is filtered and washed with EtOAc (3×20 mL). The filtrate is evaporated in vacuo and is purified by flash chromatography to give the product as an off white solid (120 mg, 21%): mp 77-79° C.; 1H NMR (CDCl3) 1.71 (m, 2 H), 2.15 (m, 3 H), 2.40 (bs, 1 H), 2.62 (m, 4 H), 2.72 (m, 1 H), 2.83 (m, 2 H), 7.27-7.81 (m, 9 H).

Workup

  1. temperatureis refluxed for 12 hr
  2. filtrationThe mixture is filtered
  3. washwashed with EtOAc (3×20 mL)
  4. customThe filtrate is evaporated in vacuo
  5. customis purified by flash chromatography

Sources & evidence

ORD record
ord-4a00164c47504bdaad28e23837c1b8e5
Source dataset
uspto-grants-2000_10
Patent number
US06130234

Reaction notes

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