Potassium Carbonate → 1-(3-Butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidine

HRID 1279365Notes

Reaction equation

HRID 1279365 reaction equation
S([CH2:5][CH2:6][C:7]#[CH:8])(C)(=O)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([OH:22])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:5]([N:19]1[CH2:18][CH2:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)([OH:22])[CH2:21][CH2:20]1)[CH2:6][C:7]#[CH:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 12053774192989-95-0

Product 1

HCID 222257381-(3-Butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidineYield 87.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-mesylbut-3-yne (1.48 g, 10.0 mmol), 4-(4-chlorophenyl)-4-hydroxypiperidine (2.54 g, 12.0 mmol) and K2CO3 (4.14 g, 30.0 mmol) in CH3CN (25 mL) 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 (2.30 g, 87%): mp 98-100° C.; 1H NMR (CDCl3) 1.55 (s, 1 H), 1.74 (m, 2 H), 1.99 (m, 1 H), 2.10 (m, 2 H), 2.42 (m, 4 H), 2.65 (m, 2 H), 2.79 (m, 2 H), 7.32 (d, J=7.2 Hz, 2 H), 7.42 (d, J=7.2 Hz, 2 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-0ba116bcc3c644f09ac3ea1e19654397
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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