Acetylene → HCID 19895456, compound

HRID 892453Notes

Reaction equation

HRID 892453 reaction equation
C#C.[CH3:3][C:4](C)([O-])C.[K+].[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]2)=[CH:12][CH:11]=1.[Cl-:34].[NH4+]>O1CCCC1>[ClH:34].[C:3]([C:23]1([OH:26])[CH2:22][CH2:21][N:20]([CH2:19][CH2:18][CH2:17][CH:16]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)[CH2:25][CH2:24]1)#[CH:4]

Participants

6

Reactant 4

HCID 6326Acetylene2×HCID 25517Ammonium ChlorideHCID 19895458HCID 19895458, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19895456HCID 19895456, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

Acetylene is introduced into a solution containing 38.4 g of potassium tert-butoxide in 250 ml of tetrahydrofuran at a temperature between 0° C. and -5° C. under stirring for 30 minutes, then 78.0 g of 1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidone dissolved in 200 ml of tetrahydrofuran are dropwise added and acetylene is introduced for an additional one hour. Thereafter the reaction mixture is cooled to -10° C. and saturated aqueous ammonium chloride solution is added under nitrogen. After evaporating tetrahydrofuran under reduced pressure, the residue is extracted with benzene. The benzene solution is washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. After taking up the residue in acetone, the hydrochloride is precipitated by adding hydrogen chloride in diisopropyl ether solution. The title hydrochloride is obtained in 91.0% yield, m.p.: 166°-168° C.

Workup

  1. additionare dropwise added
  2. customAfter evaporating tetrahydrofuran under reduced pressure
  3. extractionthe residue is extracted with benzene
  4. washThe benzene solution is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customthe hydrochloride is precipitated
  8. additionby adding hydrogen chloride in diisopropyl ether solution

Sources & evidence

ORD record
ord-3c2c160ab3574263bdbf74cc380ef59c
Source dataset
uspto-grants-1992_06
Patent number
US05118687

Reaction notes

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