4,4'-Bipiperidine dihydrochloride → 4,4'-Bipiperidine, 1-boc protected

HRID 494014Notes

Reaction equation

Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:5][CH2:4]1.[C:15](OC([O-])=O)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>C(O)C.[OH-].[Na+]>[NH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 10 °C

Procedure

A solution is prepared of 41 g (0.17 M) of 4,4′-bipiperidine dihydrochloride in 250 ml of ethanol and 250 ml of 2N sodium hydroxide. A solution of 18.5 g (0.085 M) of t-butyl dicarbonate in 100 ml of ethanol are added slowly, at 0° C. The reaction mixture is agitated for 1 hour at 10° C. and the ethanol is then removed by an evaporator, under reduced pressure. The residual aqueous phase is saturated with sodium chloride and extracted with ethyl acetate. The organic phase obtained is dried over magnesium sulphate and concentrated under reduced pressure. The crude product is purified by silica gel chromatography in eluting with the aid of a dichloromehane/methanol/aqueous ammonia mixture (8/2/0.4; v/v/v). 16.5 g of the compound sought after are thus obtained as a white solid (yield=72%).

Workup

customthe ethanol is then removed by an evaporator, under reduced pressure
extractionextracted with ethyl acetate
customThe organic phase obtained
dry with materialis dried over magnesium sulphate
concentrationconcentrated under reduced pressure
customThe crude product is purified by silica gel chromatography
washin eluting with the aid of a dichloromehane/methanol/aqueous ammonia mixture (8/2/0.4; v/v/v)

Sources & evidence

ORD record: ord-c75086f5b7984dd5a4371536ebd168c0
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538111B2

Reaction notes

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