Hydrochloric Acid → 4-Methylamino-4-phenylcyclohexanone

HRID 1095495Notes

Reaction equation

HRID 1095495 reaction equation
Cl.[CH3:2][NH:3][C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH2:6][CH2:5]1>O>[CH3:2][NH:3][C:4]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:13][CH2:12][C:7](=[O:8])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12595582Methyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine

Product 1

HCID 133452704-Methylamino-4-phenylcyclohexanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of conc. HCl (15 ml) and water (8 ml) was poured over methyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine (2.1 g, 8.4 mmol) and the mixture was stirred at RT for 5 days. For working up, the reaction mixture was diluted with water (20 ml) and extracted with ether (3×30 ml). The ethereal phase was discarded. The aqueous phase was then rendered basic with 2N NaOH and extracted with methylene chloride (3×30 ml). The organic phase obtained in this way was dried with Na2SO4 and then concentrated on a rotary evaporator. By purification by chromatography on silica gel with ethyl acetate/ethanol (4:1), it was possible to obtain the ketone Ket-15 in a yield of 1.38 g (81%) as a solid with a melting point of 32-38° C.

Workup

  1. extractionextracted with ether (3×30 ml)
  2. extractionextracted with methylene chloride (3×30 ml)
  3. customThe organic phase obtained in this way
  4. dry with materialwas dried with Na2SO4
  5. concentrationconcentrated on a rotary evaporator
  6. customBy purification by chromatography on silica gel with ethyl acetate/ethanol (4:1), it

Sources & evidence

ORD record
ord-0e30f70f5fc84e518f06095e46acd990
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…