HCID 86594056, compound → 4-Dimethylamino-4-phenyl-cyclohexylamine

HRID 1179084Notes

Reaction equation

HRID 1179084 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6](=[N:9]O)[CH2:5][CH2:4]1>CO.[OH-].[Na+].O>[CH3:1][N:2]([CH3:17])[C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][CH:6]([NH2:9])[CH2:5][CH2:4]1

Participants

5

Reactant 1

HCID 86594056HCID 86594056, compound

Product 1

HCID 129862564-Dimethylamino-4-phenyl-cyclohexylamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Dimethylamino-4-phenyl-cyclohexanone oxime (11 g) was dissolved in methanol (200 ml) and diluted with 5M NaOH (200 ml). Devarda alloy (30 g) was added in portions to this mixture. The reaction temperature here was between 50-60° C. 15 minutes after completion of the addition, the mixture was diluted with water (150 ml), methanol was removed in vacuo, and the aqueous solution was extracted with ether (5×50 ml). The combined extracts were dried over Na2SO4 and concentrated. N,N-Dimethyl-1-phenylcyclohexane-1,4-diamine was obtained as a yellow oil (10.0 g).

Workup

  1. additionDevarda alloy (30 g) was added in portions to this mixture
  2. customhere was between 50-60° C
  3. addition15 minutes after completion of the addition
  4. customwas removed in vacuo
  5. extractionthe aqueous solution was extracted with ether (5×50 ml)
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-134788cf338e491ea99c66cc773ad06f
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

Loading…