Sodium Hydroxide → 1-Methyl-4-piperidinemethanol

HRID 2377243Notes

Reaction equation

HRID 2377243 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[CH2:13][CH2:12][CH:11]([C:14](OCC)=[O:15])[CH2:10][CH2:9]1.[OH-].[Na+]>O1CCCC1>[CH3:7][N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 11062856Ethyl 1-methylpiperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2719711-Methyl-4-piperidinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of lithium aluminum hydride (0.88 g, 23 mmol) in tetrahydrofuran (50 mL) was added dropwise a solution of Example 59 (1.03 g, 6 mmol) in tetrahydrofuran (10 mL) and the mixture was heated to reflux for about 2 hours. The mixture was cooled to about 0° C. and saturated aqueous sodium hydroxide (3.5 mL) was added dropwise. After stirring for about 10 minutes at room temperature, the mixture was filtered, the filter cake was washed with tetrahydrofuran and the combined filtrates were dried (Na2SO4), filtered and concentrated under vacuum to provide the desired product. 1H NMR (500 MHz, CDCl3): δ 1.10 (m, 1H), 1.60-2.00 (m, 4H), 2.10 (m, 2H), 2.28 (s, 3H), 2.65 (m, 1H), 2.82 (m, 1H), 3.57 (dd, J=8, 14 Hz, 1H), 3.63 (dd, J=8, 14 Hz, 1H), 3.70 (m, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for about 2 hours
  3. filtrationthe mixture was filtered
  4. washthe filter cake was washed with tetrahydrofuran
  5. dry with materialthe combined filtrates were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c33a99ba865d417bb4ca724cb44917bf
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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