Water → 4-amino-1-methyl-4-Piperidinemethanol

HRID 1734569Notes

Reaction equation

HRID 1734569 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1([C:15](O)=[O:16])[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1.O.[OH-].[Na+]>O1CCCC1>[NH2:7][C:8]1([CH2:15][OH:16])[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2729544-Amino-1-methylpiperidine-4-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 152917354-amino-1-methyl-4-PiperidinemethanolYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride powder (15.62 g., 0.412 mole) in dry tetrahydrofuran (THF) (600 ml.) was heated under reflux for 15 minutes, after which 4-amino-1-methylpiperidine-4-carboxylic acid (31.0 g., 0.196 mole) in the form of a dry powder was added portionwise under nitrogen, with efficient stirring. After the addition was completed, the reaction mixture was heated under reflux for four hours, cooled to 0° C. under nitrogen with efficient stirring, worked up by careful slow addition of water (20 ml.), 15% aqueous NaOH (20 ml.) and again water (10 ml.). The reaction mixture was filtered and the precipitate was extracted with boiling THF (3 ×150 ml.). The THF liltrate and the extracts were combined and the solvent removed at 25 mm to give a yellow viscous oil (28.0 g., 98.9% yield).

Workup

  1. temperatureunder reflux for 15 minutes
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for four hours
  5. filtrationThe reaction mixture was filtered
  6. extractionthe precipitate was extracted with boiling THF (3 ×150 ml.)
  7. customthe solvent removed at 25 mm
  8. customto give a yellow viscous oil (28.0 g., 98.9% yield)

Sources & evidence

ORD record
ord-86056c785d4a4e1b8a867334cb8ef9a8
Source dataset
uspto-grants-1996_07
Patent number
US05534520

Reaction notes

Loading…