benzyl N-[1-(2-fluoropentyl)piperidin-4-yl]carbamate → 1-(2-Fluoropentyl)piperidin-4-amine

HRID 445990Notes

Reaction equation

HRID 445990 reaction equation
[F:1][CH:2]([CH2:21][CH2:22][CH3:23])[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10]C(=O)OCC2C=CC=CC=2)[CH2:6][CH2:5]1>[Pd].CO>[F:1][CH:2]([CH2:21][CH2:22][CH3:23])[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH2:10])[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 71293837benzyl N-[1-(2-fluoropentyl)piperidin-4-yl]carbamate

Product 1

HCID 866782421-(2-Fluoropentyl)piperidin-4-amineYield 134.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of the chiral form (with a shorter retention time) of benzyl N-[1-(2-fluoropentyl)piperidin-4-yl]carbamate obtained in Example 1c (318 mg, 0.986 mmol), 10% Pd/C (100 mg) and methanol (7 ml) was stirred at room temperature for two hours under a hydrogen atmosphere. The atmosphere in the reaction vessel was replaced with nitrogen, 10% Pd/C was filtered off, and the solvent was distilled off to give the title compound (249 mg).

Workup

  1. filtrationwas filtered off
  2. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-4f3e6e5ea5a74e1e9df4f15ff8a1b3f6
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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