Potassium Carbonate → 1-(3,3-Diphenyl-2-propenyl)-4-ethynyl-4-hydroxypiperidine

HRID 892454Notes

Reaction equation

HRID 892454 reaction equation
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH2:9]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([C:19]1([OH:25])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)#[CH:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH2:9][N:22]2[CH2:23][CH2:24][C:19]([C:17]#[CH:18])([OH:25])[CH2:20][CH2:21]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123465451,1'-(3-Bromoprop-1-ene-1,1-diyl)dibenzeneHCID 198955804-Ethynylpiperidin-4-ol

Product 1

HCID 198955791-(3,3-Diphenyl-2-propenyl)-4-ethynyl-4-hydroxypiperidineYield 68.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 16.5 g of 3,3-diphenyl-2-propenyl bromide in 70 ml of acetone is added dropwise to a mixture of 7.5 g of 4-ethynyl-4-hydroxypiperidine, 8.5 g of anhydrous potassium carbonate and 75 ml of anhydrous acetone at room temperature over 45 minutes, then the reaction mixture is stirred at room temperature for one hour. After filtering off the inorganic salts the solution is evaporated under reduced pressure. The residue is taken up in benzene, washed with water, dried over anhydrous sodium sulfate and the solution is evaporated under reduced pressure. After recrystallizing the residue from acetonitrile the title product is obtained in 68.4% yield, m.p.: 122°-123° C.

Workup

  1. filtrationAfter filtering off the inorganic salts the solution
  2. customis evaporated under reduced pressure
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solution is evaporated under reduced pressure
  6. customAfter recrystallizing the residue from acetonitrile the title product
  7. customis obtained in 68.4% yield, m.p.: 122°-123° C.

Sources & evidence

ORD record
ord-5f369cdad977427d99623ea62f2a215c
Source dataset
uspto-grants-1992_06
Patent number
US05118693

Reaction notes

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