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

HRID 1948603Notes

Reaction equation

HRID 1948603 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-fluorophenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-dimethylamine hydrochloride (7.2 g, 22.75 mmole) was dissolved in water (9.6 ml), conc. hydrochloric acid (14 ml, 455 mmole) was added and the mixture was stirred for 4 days at room temperature. After completion of the hydrolysis the reaction mixture was extracted with diethyl ether (2×50 ml), the aqueous phase was make alkaline with 5N sodium hydroxide solution while cooling with ice, whereupon the product precipitated out. The ketone Ket-7 was isolated as a yellow solid with a melting point of 83°-88° C. and in a yield of 50% (6.05 g).

Workup

  1. customAfter completion of the hydrolysis the reaction mixture
  2. extractionwas extracted with diethyl ether (2×50 ml)
  3. temperaturewhile cooling with ice, whereupon the product
  4. customprecipitated out

Sources & evidence

ORD record
ord-744651ae5fd741a6bca4bc5fe9a23ef5
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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