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

HRID 1250695Notes

Reaction equation

HRID 1250695 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-tetrahydropyrdin-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 capparatus 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; 1H NMR (CDCl3) d 1.49 (s, 9H), 1.64 (m, 2H), 1.86 (bd, 2H, J=13.4 Hz), 2.88 (bt, 2H, J=14 Hz), 3.14 (tt, 1H, J=12 Hz, J=4 Hz), 4.27 (bs, 2H), 7.31 (m, 2H), 7.56 (bt, 1H, J=7.7 Hz), 7.63 (bd, 1H, J=7.7 Hz).

Workup

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

Sources & evidence

ORD record
ord-39941b7a8fd549bda75238eeba5982b6
Source dataset
uspto-grants-2002_01
Patent number
US06339090B1

Reaction notes

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