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

HRID 76929
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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
  • extractionextracted with dichloromethane three times
  • washThe organic phase was washed with a little water
  • dry with materialdried over Na2SO4
  • concentrationconcentrated to low volume in a vacuum
  • Sources & evidence

    ORD record
    ord-139fa66645ef4da2beb0df6d962c5f50
    Source dataset
    uspto-grants-2014_09
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08835689B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes