Hydrochloric Acid → 3-Cyclohexanecarbonyl-8-methyl-3,8-diazabicyclo[3.2.1]octane

HRID 1605941Notes

Reaction equation

[CH:1]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.C1(C(Cl)=O)CCCCC1.Cl.Cl.[CH3:25][N:26]1[CH:31]2[CH2:32][CH2:33][CH:27]1[CH2:28][NH:29][CH2:30]2.[OH-].[Na+].Cl>O.C(Cl)(Cl)Cl>[CH:1]1([C:7]([N:29]2[CH2:30][CH:31]3[N:26]([CH3:25])[CH:27]([CH2:33][CH2:32]3)[CH2:28]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

Cyclohexane carboxylic acid (1.29 g, 0.010 mole) and 1.2 g (0.010 mole) thionyl chloride were heated in a dry atmosphere at 90° C for 1 hour. To this cyclohexane carboxylic acid chloride, at 0° C, was added a mixture of 2.0 g (0.010 mole) 8-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (prepared as described in Example 1), 1.6 g sodium hydroxide dissolved in 16 ml water, and 16 ml chloroform which had been stirred vigorously at room temperature and then chilled to 0° C. The reaction was stirred at 0° C for 1 hour. The crude product was isolated as a yellow oil by extraction of the aqueous phase with chloroform. Purification by chromatography on alumina followed by treatment with ethanolic hydrogen chloride yielded 1.58 g (58% yield) of the desired product as a white monohydrochloride, melting point 263°-268° C.

Workup

customPurification by chromatography on alumina

Sources & evidence

ORD record: ord-7e29de604b14497287e70336e8285ae3
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03951980

Reaction notes

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