{1-[2-(4-Fluorophenyl)ethyl]-piperidin-3-ylmethyl}carbamic Acid Benzyl Ester → C-{1-[2-(4-Fluorophenyl)ethyl]-piperidin-3-yl}methylamine

HRID 896532Notes

Reaction equation

HRID 896532 reaction equation
C(OC(=O)[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:13]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][N:14]2[CH2:15][CH2:16][CH2:17][CH:12]([CH2:11][NH2:10])[CH2:13]2)=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 69738345{1-[2-(4-Fluorophenyl)ethyl]-piperidin-3-ylmethyl}carbamic Acid Benzyl Ester

Product 1

HCID 10728523C-{1-[2-(4-Fluorophenyl)ethyl]-piperidin-3-yl}methylamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of {1-[2-(4-fluorophenyl)ethyl]-piperidin-3-ylmethyl}carbamic acid benzyl ester (140 mg, 370 μmol) was combined with Pearlman's catalyst (50 mg) and methanol (10 mL) and shaken under an atmosphere of hydrogen (40 psig) for 17 hours. The mixture was filtered, and the filtrate was concentrated to provide a gum (88 mg, quantitative) which was used without further purification. 1H NMR (300 MHz, CD3OD) δ7.21 (m, 2H), 6.99 (t, J=9 Hz, 2H), 3.1-2.9 (m, 2H), 2.80 (m, 2H), 2.60 (m, 2H), 2.1-1.0 (m, 9H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto provide a gum (88 mg, quantitative) which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-558faceca58a4b5a881a77a7aed32b88
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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