Acetic Acid → Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylate

HRID 429871

Reaction equation

HRID 429871 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 18326592tert-butyl 4-(2-cyanophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 18326585Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of 2-[1-tert-butoxycarbonyl-(1,2,3,6-tetrahydropyridin-4-yl)]benzonitrile (5.3 g, 0.019 mol) and acetic acid (0.28 ml, 4.9 mmol) in ethanol (200 ml), degassed with argon was added palladium on carbon. The reaction was hydrogenated on a Parr apparatus at 50 psi for 15 hours. The mixture was recharged twice with acetic acid (0.14 ml, 0.28 ml) and palladium on carbon (900 mg, 1.8 g), hydrogenated as above and filtered through celite. Solvent evaporation gave 2-(1-tert-butoxycarbonylpiperidin-4-yl)benzonitrile.

Workup

  1. filtrationhydrogenated as above and filtered through celite
  2. customSolvent evaporation

Sources & evidence

ORD record
ord-c8ef6b5bd68c4fa685ac8b21b530cc74
Source dataset
uspto-grants-2001_11
Patent number
US06319932B1

Linked notes

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