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

HRID 1095487Notes

Reaction equation

HRID 1095487 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-oneYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[8-(3-Fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-dimethyl-amine hydrochloride (7.2 g, 22.75 mmol) was dissolved in water (9.6 ml), concentrated hydrochloric acid (14 ml, 455 mmol) was added and the mixture was stirred at room temperature for 4 d. When the hydrolysis had ended, the reaction mixture was extracted with diethyl ether (2×50 ml) and the aqueous phase was rendered alkaline with 5 N sodium hydroxide solution, while cooling with ice, during which the product precipitated out. It was possible to isolate the ketone Ket-13 as a yellow solid with a melting point of 83-88° C. and a yield of 50% (6.05 g).

Workup

  1. extractionthe reaction mixture was extracted with diethyl ether (2×50 ml)
  2. temperaturewhile cooling with ice, during which the product
  3. customprecipitated out

Sources & evidence

ORD record
ord-7b10028a3d884153aa58a53025b88dd1
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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