4-(4'-Cyanophenyl)piperidine → HCID 19391376, compound

HRID 1757001Notes

Reaction equation

HRID 1757001 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[CH3:15][O:16][C:17]([CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26](OC2C=CC([N+]([O-])=O)=CC=2)=[O:27])[CH2:22][CH2:21]1)=[O:18]>C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:26]([N:23]3[CH2:24][CH2:25][CH:20]([CH2:19][C:17]([O:16][CH3:15])=[O:18])[CH2:21][CH2:22]3)=[O:27])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 27579714-(4'-Cyanophenyl)piperidineHCID 19391538HCID 19391538, compound

Product 1

HCID 19391376HCID 19391376, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.3 g of 4-(4-cyanophenyl)-piperidine and 2.9 g of 4-(methoxycarbonylmethyl)-1-[(4-nitrophenyl)-oxycarbonyl]-piperidine are stirred at 140° C. for 2.5 hours. The mixture is left to cool and the residue is dissolved in ethyl acetate. The organic phase is washed twice with 0.5N sodium hydroxide solution and once with water. The ethyl acetate phase is dried over sodium sulphate and the solvent is removed under reduced pressure. The residue remaining is chromatographed over silica gel. Yield: 1.5 g (58% of theory), Melting point: 115°-118° C. Rf value: 0.32 (silica gel; ethyl acetate/cyclohexane=1:1)

Workup

  1. waitThe mixture is left
  2. temperatureto cool
  3. washThe organic phase is washed twice with 0.5N sodium hydroxide solution and once with water
  4. dry with materialThe ethyl acetate phase is dried over sodium sulphate
  5. customthe solvent is removed under reduced pressure
  6. customThe residue remaining is chromatographed over silica gel

Sources & evidence

ORD record
ord-c6bf956822fd4b3284b76769881eb0ec
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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