Sodium Hydroxide → (1,4-Dimethylpiperidin-4-yl)methanol

HRID 60299Notes

Reaction equation

HRID 60299 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][C:6]([CH3:12])([C:9](O)=[O:10])[CH2:5][CH2:4]1.[AlH4-].[Li+].[OH-].[Na+]>O1CCCC1.O.C(OCC)C>[CH3:2][N:3]1[CH2:8][CH2:7][C:6]([CH2:9][OH:10])([CH3:12])[CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 455953381,4-Dimethylpiperidine-4-carboxylic acid hydrochloride

Product 1

HCID 20646825(1,4-Dimethylpiperidin-4-yl)methanolYield 73.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 1,4-dimethylpiperidine-4-carboxylic acid hydrogen chloride (1.00 g, 5.17 mmol) in tetrahydrofuran (18.9 mL) was added lithium tetrahydroaluminate (1.0N solution in tetrahydrofuran, 20.7 mL, 20.7 mmol) dropwise over 5 minutes. The reaction mixture was stirred at ambient temperature for 12 hours and then diluted with water (20 mL), basified to pH ˜12 by addition of sodium hydroxide pellets, and then diluted with diethyl ether (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a colorless oil (543 mg, 73%). 1H NMR (400 MHz, d6-DMSO) δ 4.44 (m, 1H), 3.12 (d, J=5.4, 2H), 2.50 (m, 2H), 2.39-2.31 (m, 2H), 2.13 (s, 3H), 2.12-2.09 (m, 1H), 1.42 (m, 2H), 1.16 (m, 2H), 0.82 (s, 3H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70f093588dc54d528f1e39880060ca94
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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