Sodium Hydroxide → HCID 69216446, compound

HRID 1394284Notes

Reaction equation

HRID 1394284 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.C(OP([CH2:25][C:26]#[N:27])(=O)OCC)C.[OH-].[Na+]>C(Cl)Cl>[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[CH:25][C:26]#[N:27])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 69216446HCID 69216446, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Dimethylamino-4-phenyl-cyclohexanone (10.85 g, 50 mmole) and cyanomethanephosphonic acid diethyl ester (10.65 g, 12 mmole) were dissolved in DCM (100 ml). This solution was added dropwise with ice water cooling at a temperature of 5 to 10° C. with vigorous stirring to a solution of 40% aqueous NaOH (50 ml) and stirred for 2 h at RT. Working up was performed by combining the batch with ice (100 g). The organic phase was separated off. The aqueous phase was extracted with DCM (3×40 ml). The combined extracts were washed with saturated NaCl-solution (50 ml), dried over Na2SO4 and then evaporated. (4-Dimethylamino-4-phenylcyclohexylidene)acetonitrile was obtained as a yellow oil in a yield of 95% (11.4 g).

Workup

  1. customThe organic phase was separated off
  2. extractionThe aqueous phase was extracted with DCM (3×40 ml)
  3. washThe combined extracts were washed with saturated NaCl-solution (50 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-ad29133ca8d648b8841359ddf9d0f9de
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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