Water → trans-{4-(Benzyl-methyl-amino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-yl}-methanol

HRID 896553Notes

Reaction equation

HRID 896553 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:11]([N:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:13])[CH2:10][CH2:9][N:8]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:14]([N:12]([CH3:13])[C@@H:11]1[CH2:10][CH2:9][N:8]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:7][C@H:6]1[CH2:4][OH:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69737831HCID 69737831, compound

Product 1

HCID 69736397trans-{4-(Benzyl-methyl-amino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-yl}-methanolYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of trans-4-(benzyl-methyl-amino)-1-[2-(4-fluorophenyl)-ethyl]-piperidine-3-carboxylic acid ethyl ester (144 mg, 361 μmol) in tetrahydrofuran (1 mL) was treated with a solution of lithium aluminum hydride (1.0 M in tetrahydrofuran, 723 μL, 723 μmol). The mixture was stirred at room temperature for 2.5 hours, then was treated very slowly with 28 μL of water, followed by 28 μL of 15% aqueous sodium hydroxide, then by 84 μL of water. The mixture was filtered and the solid was washed with ether. The filtrate and washes were combined and concentrated under vacuum to provide a white solid (116 mg, 90%). 1H NMR (300 MHz, CDCl3) δ7.34 (m, 5H), 7.15 (m, 2H), 6.98 (t, J=9 Hz, 2H), 6.26 (bs, 1H), 3.78 (d, J=13 Hz, 1H), 3.60 (m, 2H), 3.50 (m, 1H), 3.10 (m, 1H), 2.87 (m, 1H), 2.78 (m, 2H), 2.54 (m, 2H), 2.28 (s, 3H), 2.20 (m, 1H), 1.88 (m, 2H), 1.75 (m, 1H), 1.58 (m, 1H). Mass spec (ES+) m/z 357.3 (M+H+).

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with ether
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7f094ab882434a29a14b18d9818ba24c
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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