Hydrochloric Acid → (RS)-1,4-Dibenzyl-piperidin-3-one

HRID 382790Notes

Reaction equation

C(OC([C:6]1([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][C:7]1=[O:19])=O)C.Cl.[OH-].[Na+]>C(O)C>[CH2:12]([N:9]1[CH2:10][CH2:11][CH:6]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:7](=[O:19])[CH2:8]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 13.5 g (SR)-1,4-dibenzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (38.4 mmol) in 20 ml ethanol were added 47.5 ml HCl (37%) and the yellow solution was refluxed for 48 h. The reaction mixture was cooled to 0° C. and NaOH was added until pH 8 was reached. The aqueous phase was extracted three times with ethyl acetate (200 ml) and the combined organic phases were washed with water (2×100 ml) and brine (2×100 ml). The organic phase was dried over MgSO4, filtrated and the solvent was removed under reduced pressure to give 9.8 g of the product (35 mmol, 91%) as a brown oil.

Workup

temperaturethe yellow solution was refluxed for 48 h
extractionThe aqueous phase was extracted three times with ethyl acetate (200 ml)
washthe combined organic phases were washed with water (2×100 ml) and brine (2×100 ml)
dry with materialThe organic phase was dried over MgSO4
filtrationfiltrated
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-3f5bc7b8dd4d4de491999b03846f0c50
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310213B1

Reaction notes

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