Hydrochloric Acid → 4-(1-Dimethylamino-3-phenylpropyl)-cyclohexanone

HRID 12644Notes

Reaction equation

HRID 12644 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([N:20]([CH3:22])[CH3:21])[CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl.C(OCC)C.[OH-].[Na+]>O>[CH3:22][N:20]([CH3:21])[CH:11]([CH:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]1)[CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 66703150[1-(1,4-Dioxa-spiro[4.5]dec-8-yl)-3-phenylpropyl]-dimethylamine

Product 1

HCID 667034194-(1-Dimethylamino-3-phenylpropyl)-cyclohexanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude product of the ketal 7e (29.6 g, 97 mmole) was dissolved in water (44 ml), concentrated hydrochloric acid (64 ml) was added, and the mixture was stirred for 20 hours at RT. The reaction mixture was shaken with diethyl ether (2×100 ml), the aqueous phase was made alkaline with 5N NaOH while cooling with ice, and was extracted with dichloromethane (3×100 ml), dried, and concentrated by evaporation. The ketone was isolated as a colorless oil.

Workup

  1. temperaturewhile cooling with ice
  2. extractionwas extracted with dichloromethane (3×100 ml)
  3. customdried
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ffdc3e8a32ea49aaa4d8e260f3fbe86b
Source dataset
uspto-grants-2010_06
Patent number
US07728028B2

Reaction notes

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