Sodium Hydroxide → 4-(Dimethylamino)-4-phenylcyclohexan-1-one

HRID 245585Notes

Reaction equation

HRID 245585 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH2:4]1.[OH-].[Na+]>Cl>[CH3:1][N:2]([CH3:19])[C:3]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:12][CH2:11][C:6](=[O:7])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 12595611HCID 12595611, compound

Product 1

HCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
65 °C

Procedure

The residue (N,N-dimethyl-8-phenyl-1,4-dioxaspiro-[4.5]decan-8-amine) was taken up in aqueous HCl at pH 1. It was stirred for 1 hour at 65° C. The batch was cooled and brought to pH 4 with NaOH solution. 2-MTHF (52 ml) was then added. The mixture was alkalised with NaOH at 15-25° C. to pH≧12. The organic phase was concentrated at 45° C. and at reduced pressure (<10 mbar). The residue was dissolved at 65° C. in twice the amount of isopropanol/H2O 60/40. The batch was stirred overnight at −10° C. The precipitate was suctioned off, subsequently washed with cold isopropanol/H2O and dried overnight in a drying cupboard (45° C., <100 mbar).

Workup

  1. temperatureThe batch was cooled
  2. concentrationThe organic phase was concentrated at 45° C. and at reduced pressure (<10 mbar)
  3. dissolutionThe residue was dissolved at 65° C. in twice the amount of isopropanol/H2O 60/40
  4. stirringThe batch was stirred overnight at −10° C
  5. washsubsequently washed with cold isopropanol/H2O
  6. customdried overnight in a drying cupboard (45° C., <100 mbar)

Sources & evidence

ORD record
ord-ead49d0dfade467a80f56cb45a283d42
Source dataset
uspto-grants-2014_02
Patent number
US08658827B2

Reaction notes

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