Potassium Carbonate → 4-Benzyl-1-(3-butynyl)-4-hydroxypiperidine

HRID 1279378Notes

Reaction equation

HRID 1279378 reaction equation
S([CH2:5][CH2:6][C:7]#[CH:8])(C)(=O)=O.[CH2:9]([C:16]1([OH:22])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:9]([C:16]1([OH:22])[CH2:21][CH2:20][N:19]([CH2:8][CH2:7][C:6]#[CH:5])[CH2:18][CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 981524-Benzyl-4-piperidinolHCID 12053774192989-95-0

Product 1

HCID 106817044-Benzyl-1-(3-butynyl)-4-hydroxypiperidineYield 86.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-mesylbut-3-yne (1.63 g, 11.0 mmol), 4-benzyl-4-hydroxypiperidine (1.91 g, 10.0 mmol) and K2CO3 (4.14 g, 30.0 mmol) in 50 mL of CH3CN is refluxed for 12 hr. The mixture is filtered and washed with EtOAc (3×30 mL). The filtrate is evaporated in vacuo and is purified by flash chromatography to give the product as a colorless solid (2.1 g, 86%): mp 51-53° C.; 1H NMR (CDCl3) 1.50 (m, 2 H), 1.65 (m, 3 H), 1.97 (s, 1 H), 2.35 (m, 4 H), 2.62 (m, 4 H), 2.75 (s, 1 H), 7.21-7.31 (m, 5 H).

Workup

  1. temperatureis refluxed for 12 hr
  2. filtrationThe mixture is filtered
  3. washwashed with EtOAc (3×30 mL)
  4. customThe filtrate is evaporated in vacuo
  5. customis purified by flash chromatography

Sources & evidence

ORD record
ord-2e50266266414ba88281c3edaf6ee90a
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

Loading…