Dimethyl-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-ylmethyl)-amine → 4-Dimethylaminomethyl-4-phenylcyclohexanone

HRID 76929Notes

Reaction equation

HRID 76929 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH2:6][CH2:5]1>OS(O)(=O)=O>[CH3:20][N:2]([CH2:3][C:4]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:5][CH2:6][C:7](=[O:8])[CH2:12][CH2:13]1)[CH3:1]

Participants

3

Reactant 1

HCID 45026964Dimethyl-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-ylmethyl)-amine

Product 1

HCID 686322734-Dimethylaminomethyl-4-phenylcyclohexanone

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The title compound of step 5 (5.40 g, 19.6 mmol) was dissolved in 5% H2SO4 (300 mL) and stirred for 1 d at RT. The solution was then washed with ether three times and the ether phase discarded. The aqueous phase was made alkaline with 5N NaOH with ice cooling and extracted with dichloromethane three times. The organic phase was washed with a little water, dried over Na2SO4 and concentrated to low volume in a vacuum.

Workup

  1. washThe solution was then washed with ether three times
  2. extractionextracted with dichloromethane three times
  3. washThe organic phase was washed with a little water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to low volume in a vacuum

Sources & evidence

ORD record
ord-139fa66645ef4da2beb0df6d962c5f50
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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