1-Benzyl-4-piperidone → HCID 19959214, compound

HRID 54536Notes

Reaction equation

HRID 54536 reaction equation
[Br-].[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].CC(C)([O-])C.[K+].[CH2:33]([N:40]1[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1>[CH2:33]([N:40]1[CH2:45][CH2:44][C:43](=[CH:7][CH2:6][CH2:5][CH2:4][C:2]#[N:3])[CH2:42][CH2:41]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 11418829(4-Cyanobutyl)(triphenyl)phosphanium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 19959214HCID 19959214, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 4-cyanobutyltriphenylphosphonium bromide (21.80 g) in tetrahydrofuran (100 ml) was added potassium tert-butoxide (5.76 g) in tetrahydrofuran (50 ml) over 30 minutes at 0° C. After 1 hour, a solution of 1-benzyl-4-piperidone (8.84 g) was added to the mixture over 30 minutes at 0° C. The mixture was stirred at ambient temperature for 1 hour, poured into ice-water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on alumina eluting with chloroform/hexane (1:1) and the fractions containing the object compound were combined and evaporated to afford 1-benzyl-4-(4-cyanobutylidene)piperidine (9.8 g) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on alumina eluting with chloroform/hexane (1:1)
  6. additionthe fractions containing the object compound
  7. customevaporated

Sources & evidence

ORD record
ord-cb2d068c245b40a9bd290c5985f276cd
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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