Diethyl Ether → Dimethyl-(4-methylene-1-phenyl-cyclohexyl)-amine

HRID 1477180Notes

Reaction equation

[CH3:1]COCC.[CH3:6][N:7]([CH3:21])[C:8]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:6][N:7]([CH3:21])[C:8]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][C:11](=[CH2:1])[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 40 °C

Procedure

Tert-BuOK (0.550 g, 4.74 mmol) was provided in abs. ether (10 mL) in argon and methyl triphenyl phosphonium bromide (1.89 g, 4.74 mmol) added. The mixture was then heated to 40° C. for 30 min. After this reaction time 4-dimethylamino-4-phenylcyclohexanone (1.00 g, 4.60 mmol) dissolved in abs. THF (10 mL) was carefully added in drops and the reaction solution was heated to 50° C. for 5 h. The reaction batch was stirred overnight at room temperature and concentrated in a vacuum until dry. The residue was taken up in dioxan (50 mL) and mixed with HCl/dioxan (5 mL). The precipitated solid was aspirated and washed with ether. The isolated hydrochloride was basified with 2 N NaOH and extracted with dichloromethane (2×80 mL). The organic phase was dried over Na2SO4, filtered and concentrated to low volume in a vacuum.

Workup

temperaturethe reaction solution was heated to 50° C. for 5 h
concentrationconcentrated in a vacuum
customuntil dry
additionmixed with HCl/dioxan (5 mL)
washwashed with ether
extractionextracted with dichloromethane (2×80 mL)
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated to low volume in a vacuum

Sources & evidence

ORD record: ord-5680e31471f74add8e2ad8752f9ad441
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403767B2

Reaction notes

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