Potassium Carbonate → 4-(4-Chlorobenzyl)-1-(3-butynyl)piperidine

HRID 1279380Notes

Reaction equation

HRID 1279380 reaction equation
S([CH2:5][CH2:6][C:7]#[CH:8])(C)(=O)=O.Cl.[Cl:10][C:11]1[CH:23]=[CH:22][C:14]([CH2:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][CH:16]2[CH2:17][CH2:18][N:19]([CH2:8][CH2:7][C:6]#[CH:5])[CH2:20][CH2:21]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12053774192989-95-0HCID 170395664-[(4-Chlorophenyl)methyl]piperidine--hydrogen chloride (1/1)

Product 1

HCID 106828724-(4-Chlorobenzyl)-1-(3-butynyl)piperidineYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-mesylbut-3-yne (2.22 g, 15.0 mmol), 4-(4-chlorobenzyl)piperidine hydrochloride (2.95 g, 12.0 mmol), K2CO3 (4.97 g, 36.0 mmol) in 50 mL of CH3CN is allowed to reflux for 12 hr. The inorganic salt is removed through a short column of silica gel and washed with EtOAc (3×30 mL). Evaporation of solvents gives a residue, which is purified by flash chromatography giving the product as pale yellow oil (2.67 g, 85%): 1H NMR (CDCl3) 1.31 (m, 2 H), 1.50 (m, 1 H), 1.59 (m, 2 H), 1.96 (m, 3 H), 2.38 (m, 2 H), 2.48 (m, 2 H), 2.55 (m, 2 H), 2.88 (d, J=11.1 Hz, 2 H), 7.04 (d, J=8.1 Hz, 2 H), 7.26 (d, J=8.1 Hz, 2 H).

Workup

  1. temperatureto reflux for 12 hr
  2. customThe inorganic salt is removed through a short column of silica gel
  3. washwashed with EtOAc (3×30 mL)
  4. customEvaporation of solvents
  5. customgives a residue, which
  6. customis purified by flash chromatography

Sources & evidence

ORD record
ord-351b78e226b646e1b94ca335772c68c7
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

Loading…