Hydrochloric Acid → 4-(Dimethylamino)-4-(3-fluorophenyl)cyclohexan-1-one

HRID 1948604Notes

Reaction equation

HRID 1948604 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([C:9]2([N:19]([CH3:21])[CH3:20])[CH2:18][CH2:17][C:12]3(OCC[O:13]3)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.Cl>O>[CH3:20][N:19]([CH3:21])[C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([F:2])[CH:4]=2)[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57475109HCID 57475109, compound

Product 1

HCID 574751114-(Dimethylamino)-4-(3-fluorophenyl)cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[8-(3-fluorophenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-dimethylamine hydrochloride (2.80 g, 8.86 mmole) was dissolved in water (3.7 ml), conc. hydrochloric acid (5.5 ml) was added and the mixture was stirred for 4 days at RT. After completion of the hydrolysis the reaction mixture was extracted with ether (2×10 ml), the aqueous solution was made alkaline with 5N sodium hydroxide solution while cooling with ice, the reaction mixture was extracted with dichloromethane (3×50 ml), and the organic phase was dried over sodium sulfate and concentrated by evaporation in vacuo. The crude product was purified by flash chromatography with CHCl3/MeOH (20:1).

Workup

  1. customAfter completion of the hydrolysis the reaction mixture
  2. extractionwas extracted with ether (2×10 ml)
  3. temperaturewhile cooling with ice
  4. extractionthe reaction mixture was extracted with dichloromethane (3×50 ml)
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. concentrationconcentrated by evaporation in vacuo
  7. customThe crude product was purified by flash chromatography with CHCl3/MeOH (20:1)

Sources & evidence

ORD record
ord-b1efd012fce642e69306be1999f28f6a
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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