Hydrochloric Acid → 4-Benzyl-4-dimethylaminomethyl-1-methylamino-cyclohexane carbonitrile

HRID 76932Notes

Reaction equation

[CH3:1][NH2:2].[CH2:3]([C:10]1([CH2:17][N:18]([CH3:20])[CH3:19])[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[C-:22]#[N:23].[K+]>CO.O>[CH2:3]([C:10]1([CH2:17][N:18]([CH3:20])[CH3:19])[CH2:15][CH2:14][C:13]([NH:23][CH3:22])([C:1]#[N:2])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

40% aqueous methylamine solution (15.3 mL, 121 mmol) and 4-benzyl-4-((dimethylamino)methyl)cyclohexanone (6.20 g, 25.3 mmol) dissolved in methanol (25 mL) were added to a solution of 4N hydrochloric acid (6.6 mL) and methanol (4.00 mL) cooled to 0° C. The reaction mixture was then mixed with potassium cyanide (4.00 g, 60 mmol) and stirred for 5 d at room temperature. For work up the mixture was diluted with water (180 mL) and extracted with ether (3×100 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated until dry in a vacuum.

Workup

extractionextracted with ether (3×100 mL)
dry with materialThe combined organic phases were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customuntil dry in a vacuum

Sources & evidence

ORD record: ord-2ce5109d290e4d4483de4989ceeee14b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835689B2

Reaction notes

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