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

HRID 1458767Notes

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

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 (3×15 ml.). The THF filtrate and the extracts were combined and the solvent removed at 25 mm to give a yellow viscous oil (28.0 g., 98.9% yield). IR (neat) 3320 (NH), 3200 (br. OH), 1587 (NH2), 1468, 1448 cm-1

Workup

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

Sources & evidence

ORD record: ord-ba296e07b35745cc97f84b146476147d
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05852029

Reaction notes

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