Benzyl 4-(2-oxoazepan-1-yl)piperidin-1-carboxylate → 1-(Piperidin-4-yl)azepan-2-one

HRID 20222Notes

Reaction equation

HRID 20222 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH:9]1[CH2:14][CH2:13][N:12](C(OCC2C=CC=CC=2)=O)[CH2:11][CH2:10]1>C(O)C.[Pd]>[NH:12]1[CH2:11][CH2:10][CH:9]([N:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:2]2=[O:1])[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 68418576Benzyl 4-(2-oxoazepan-1-yl)piperidin-1-carboxylate

Product 1

HCID 684175121-(Piperidin-4-yl)azepan-2-oneYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl 4-(2-oxoazepan-1-yl)piperidin-1-carboxylate (0.25 g) obtained in Example 9a) in ethanol (10 mL) was added 10% palladium on carbon (containing 50% water; 0.03 g), and the mixture was stirred at room temperature for 15 hours under a hydrogen atmosphere. The reaction mixture was filtered, and the solvent was distilled off under reduced pressure to obtain the title compound (0.15 g, quantitative) as a brown oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6fd8d293355045979e6505dd8785f092
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

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