Ammonium Chloride → HCID 66911352, compound

HRID 1011632Notes

Reaction equation

HRID 1011632 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Mg]Br)=[CH:21][CH:20]=1.[NH4+].[Cl-]>O1CCCC1.O=O>[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:8][CH2:7][C:6]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)([OH:9])[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneHCID 178491912HCID 178491912, compound

Product 1

HCID 66911352HCID 66911352, compound

Reagents, catalysts & solvents 2

HCID 977OxygenSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(dimethylamino)-4-phenylcyclohexanone (4.34 g, 20 mmol) was dissolved in absolute tetrahydrofuran (60 ml) with the exclusion of oxygen, mixed with 4-methoxy phenyl magnesium bromide solution (90 ml, 45 mmol, 0.5N) with ice cooling and boiled for 2 h with reflux. For work up the batch was mixed with saturated NH4Cl solution (50 ml) with ice cooling and stirred for 10 min at room temperature. The aqueous phase was separated off and extracted with ethyl acetate (3×25 ml). The combined organic phases were dried over Na2SO4 and then concentrated to low volume. A raw product was isolated that was purified by chromatography [silica gel 60 (50 g); ethyl acetate (1000 ml), methanol (1000 ml)]. 2.016 g (31%, mp 174-175° C.) of more non-polar and 2.51 g (39%, mp 149-151° C.) of more polar product were obtained. Both could be recrystallised from ethyl acetate.

Workup

  1. temperaturewith reflux
  2. customThe aqueous phase was separated off
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated to low volume

Sources & evidence

ORD record
ord-55a49a8152624ecca21dc49fa0be6019
Source dataset
uspto-grants-2011_07
Patent number
US07977370B2

Reaction notes

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