Dimethylamine → 4-Benzyloxy-1-dimethylaminocyclohexanecarbonitrile

HRID 1349382Notes

Reaction equation

HRID 1349382 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]([O:11][CH:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.[CH3:20][NH:21]C.[C-]#N.[K+]>CO>[CH2:4]([O:11][CH:12]1[CH2:17][CH2:16][C:15]([N:2]([CH3:3])[CH3:1])([C:20]#[N:21])[CH2:14][CH2:13]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 9032Potassium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 109873694-(Benzyloxy)cyclohexanone

Product 1

HCID 210932404-Benzyloxy-1-dimethylaminocyclohexanecarbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 130 ml of 7.9 molar aqueous dimethylamine solution, 16 ml of methanol, 20.0 g of 4-benzyloxycyclohexanone, 23.2 g of dimethylamine hydrochloride and 15.3 g of potassium cyanide was stirred for 65 hours at room temperature; extraction was carried out four times using 120 ml of diethyl ether each time, and the combined extracts were concentrated; 100 ml of dichloromethane were added to the residue, the phases were separated, and the organic phases were dried over sodium sulfate, filtered and concentrated. 24.5 g of 4-benzyloxy-1-dimethylaminocyclohexanecarbonitrile were obtained in the form of a yellowish oil which slowly solidified.

Workup

  1. extractionextraction
  2. concentrationthe combined extracts were concentrated
  3. addition100 ml of dichloromethane were added to the residue
  4. customthe phases were separated
  5. dry with materialthe organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4c61180a1d2c49dba50468e13509358b
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

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