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

HRID 1095488Notes

Reaction equation

HRID 1095488 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-Fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-dimethyl-amine hydrochloride (2.80 g, 8.86 mmol) was dissolved in water (3.7 ml), concentrated hydrochloric acid (5.5 ml) was added and the mixture was stirred at RT for 4 d. When the hydrolysis had ended, the reaction mixture was extracted with ether (2×10 ml) and the aqueous solution was rendered alkaline with 5 N sodium hydroxide solution, while cooling with ice, the reaction mixture was extracted with methylene chloride (3×50 ml) and the organic phase was dried over sodium sulfate and concentrated i. vac. The crude product was purified by flash chromatography with CHCl3/MeOH (20:1).

Workup

  1. extractionthe reaction mixture was extracted with ether (2×10 ml)
  2. temperaturewhile cooling with ice
  3. extractionthe reaction mixture was extracted with methylene chloride (3×50 ml)
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. concentrationconcentrated i
  6. customThe crude product was purified by flash chromatography with CHCl3/MeOH (20:1)

Sources & evidence

ORD record
ord-f9422388b2f649a9985db5270b378757
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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