HCID 19959214, compound → HCID 19959227, compound

HRID 54537Notes

Reaction equation

HRID 54537 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][CH2:15][CH2:16][CH2:17][C:18]#[N:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.[Pt](=O)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[N:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 19959214HCID 19959214, compound

Product 1

HCID 19959227HCID 19959227, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-benzyl-4-(4-cyanobutylidene)piperidine (8.8 g) and platinum dioxide (1.2 g) in tetrahydrofuran (150 ml) was hydrogenated at atmospheric pressure for 12 hours. After the catalyst was filtered out, the filtrate was evaporated in vacuo. The residue was chromatographed on silica gel eluting with chloroform/methanol (95:5) and the fractions containing the object compound were combined and evaporated to afford 1-benzyl-4-(4-cyanobutyl)piperidine (5.0 g) as an oil.

Workup

  1. filtrationAfter the catalyst was filtered out
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was chromatographed on silica gel eluting with chloroform/methanol (95:5)
  4. additionthe fractions containing the object compound
  5. customevaporated

Sources & evidence

ORD record
ord-6922e13dea7742429829ed26ab37aaf8
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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