Sodium Hydroxide → 2-(3-Cyano-3,3-diphenylpropyl)piperidine

HRID 974980Notes

Reaction equation

HRID 974980 reaction equation
C(O)(=O)C(O)=O.C([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[CH2:20][CH2:21][C:22]([C:35]#[N:36])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C1C=CC=CC=1.[OH-].[Na+]>C(OCC)(=O)C>[C:35]([C:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:21][CH2:20][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][NH:14]1)#[N:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 199701841-Benzyl-2-(3-cyano-3,3-diphenylpropyl)piperidine Oxalate

Product 1

HCID 199701912-(3-Cyano-3,3-diphenylpropyl)piperidineYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Benzyl-2-(3-cyano-3,3-diphenylpropyl)piperidine oxalate (3.70 g, 7.5 mmol--see Example 25) was partitioned between ethyl acetate and 0.5M aqueous sodium hydroxide solution and the organic layer was dried over magnesium sulphate and evaporated. The residue was dissolved in a mixture of acetic acid (5 ml), ethanol (5 ml) and water (2 ml) and the solution treated with sodium acetate (100 mg), palladium dichloride (100 mg) and charcoal. The mixture was stirred under 4 atmospheres of hydrogen at room temperature for 26 hours, filtered and evaporated. The residue was partitioned between ethyl acetate and 10% aqueous sodium carbonate solution and the organic layer was washed with water, dried over magnesium sulphate and evaporated to give the title compound (2.0 g, 88%) as a colourless oil which was characterised by its 1H-NMR spectrum.

Workup

  1. dry with materialthe organic layer was dried over magnesium sulphate
  2. customevaporated
  3. dissolutionThe residue was dissolved in a mixture of acetic acid (5 ml), ethanol (5 ml) and water (2 ml)
  4. additionthe solution treated with sodium acetate (100 mg), palladium dichloride (100 mg) and charcoal
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was partitioned between ethyl acetate and 10% aqueous sodium carbonate solution
  8. washthe organic layer was washed with water
  9. dry with materialdried over magnesium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-f27ad8a46667440897d9f0ec80b15646
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

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