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

HRID 1279376Notes

Reaction equation

HRID 1279376 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.[CH2:15]([C:22]1([OH:28])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:15]([C:22]1([OH:28])[CH2:27][CH2:26][N:25]([CH2:5][CH2:6][C:7]#[C:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:24][CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 981524-Benzyl-4-piperidinolHCID 184279661-Mesyl-4-phenylbut-3-yne

Product 1

HCID 184279324-Benzyl-4-hydroxy-1-(4-phenyl-3-butynyl)piperidineYield 30.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-mesyl-4-phenylbut-3-yne (300 mg, 1.34 mmol), 4-benzyl-4-hydroxypiperidine (307 mg, 1.61 mmol) and K2CO3 (555 mg, 4.02 mmol) in 15 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 (130 mg, 30%): mp 80-82° C; 1H NMR (CDCl3) 1.50 (m, 3 H), 1.74 (m, 2 H), 2.41 (m, 2 H), 2.58 (m, 3 H), 2.75 (m, 5 H), 7.11-7.38 (m, 10 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-1eb2173bf716460d87909d1928886c7b
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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