HCID 69416954, compound → HCID 69337353, compound

HRID 1179069Notes

Reaction equation

HRID 1179069 reaction equation
Cl.[CH3:2][N:3]([CH3:24])[C:4]1([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH2:6][CH2:5]1>Cl>[CH3:2][N:3]([CH3:24])[C:4]1([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:13][CH2:12][C:7](=[O:8])[CH2:6][CH2:5]1

Participants

3

Reactant 1

HCID 69416954HCID 69416954, compound

Product 1

HCID 69337353HCID 69337353, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Dimethyl-(8-naphthalen-2-yl-1,4-dioxa-spiro[4.5]dec-8-yl)-amine hydrochloride (6.09 g) was dissolved in 7.5N hydrochloric acid, stirred for 32 hours at RT and then extracted with diethyl ether (3×30 ml). The aqueous phase was rendered alkaline with 25% ammonia solution, while cooling with ice, and extracted with 1,2-dichloroethane (3×30 ml). The combined extracts were dried with Na2SO4 and concentrated. 4.48 g of 4-dimethylamino-4-naphthalen-2-yl-cyclohexanone were obtained as a white solid (m.p. 81-83° C.).

Workup

  1. extractionextracted with diethyl ether (3×30 ml)
  2. temperaturewhile cooling with ice
  3. extractionextracted with 1,2-dichloroethane (3×30 ml)
  4. dry with materialThe combined extracts were dried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-954638cd321c4cf2bd8a8cb5ad825057
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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