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

HRID 1279377Notes

Reaction equation

HRID 1279377 reaction equation
S([CH2:5][CH2:6][C:7]#[C:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=1)(C)(=O)=O.[CH2:16]([C:23]1([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:16]([C:23]1([OH:29])[CH2:28][CH2:27][N:26]([CH2:5][CH2:6][C:7]#[C:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 981524-Benzyl-4-piperidinolHCID 184279601-Mesyl-4-(3-methylphenyl)but-3-yne

Product 1

HCID 184279764-Benzyl-4-hydroxy-1-(4-(3-methylphenyl)-3-butynyl)piperidineYield 20.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-mesyl-4-(3-methylphenyl)but-3-yne (344 mg, 1.45 mmol), 4-benzyl-4-hydroxy-piperidine (332 mg, 1.73 mmol) and K2CO3 (598 mg, 4.34 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 a brown oil (100 mg, 20%): 1H NMR (CDCl3) 1.37 (s, 1 H), 1.55 (m, 2 H), 1.75 (m, 2 H), 2.30 (s, 3 H), 2.41 (m, 2 H), 2.60 (m, 3 H), 2.75 (m, 5 H), 7.11-7.31 (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-f5b8d293c71e4e44beb13571adbcd31c
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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