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

HRID 1861756Notes

Reaction equation

HRID 1861756 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:4]([N:11]1[CH2:10][CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([OH:14])[CH2:13][CH2:12]1)[CH2:3][C:2]#[CH:7]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidine

Product 1

HCID 222257381-(3-Butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidineYield 145.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixutre of 3-butyn-1-methanesulfate (1.48 g, 0.01 mol), 4-(p-chlorophenyl)-4-hydroxypiperidine (2.54 g, 0.012 mol) and potassium carbonate (4.14 g, 0.03 mol) in 25 mL of acetonitrile was refluxed for 12 hrs. The mixture was filtered and washed with ethyl acetate (3×30 mL). The filtrate was evaporated in vacuo and was purified by flash chromatography to give 2.30 g (87%) of the product as a white solid. mp 98-100° C. 1H NMR (CHCl3) 1.550 (s, 1 H), 1.749 (m, 2 H), 1.997 (m, 1 H), 2.109 (m, 2 H), 2.423 (m, 4 H), 2.655 (m, 2 H), 2.798 (m, 2 H), 7.329 (d, J=7.2 Hz, 2 H), 7.429 (d, J=7.2 Hz, 2 H).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with ethyl acetate (3×30 mL)
  3. customThe filtrate was evaporated in vacuo
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-06ef5ccfddab49bfabbb2b26e83a0a10
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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