Hydrochloric Acid → HCID 19823636, compound

HRID 728264Notes

Reaction equation

HRID 728264 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:20]([CH3:22])[CH3:21])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:19])[C:17]#N)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:23][Mg]Br.[ClH:26].[OH-:27].[Na+]>CCOCC.C1(C)C=CC=CC=1>[Cl:26][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:20]([CH3:22])[CH3:21])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:19])[C:17](=[O:27])[CH3:23])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19823821HCID 19823821, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 19823636HCID 19823636, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 6-[1-(4-chlorophenyl)cyclobutyl]-6-dimethylamino-2-methylhexanenitrile (2.25 g) in ether (15 ml) was added to a solution of methylmagnesium bromide [prepared from magnesium (0.29 g) and excess methylbromide gas in ether (20 ml)]. The mixture was stirred for one hour at 20° C. and then the ether was replaced by toluene (40 ml) and the mixture heated at 90° C. for 4 hours and then allowed to stand for 21/2 days at ambient temperature. The mixture was added to 1N hydrochloric acid (100 ml) and the mixture heated at 90°-95° C. for 30 minutes, cooled, basified with aqueous sodium hydroxide solution and extracted with ether. Removal of the ether from the dried extract gave a residue which was distilled on a Buchi Kugelrohr apparatus (170° C./0.5 mm) to give 7-[1-(4-chlorophenyl)-cyclobutyl]-7-dimethylamino-3-methylheptan-2-one.

Workup

  1. temperaturethe mixture heated at 90° C. for 4 hours
  2. custom2 days
  3. customat ambient temperature
  4. temperaturethe mixture heated at 90°-95° C. for 30 minutes
  5. temperaturecooled
  6. extractionextracted with ether
  7. customRemoval of the ether from the dried
  8. extractionextract
  9. customgave a residue which
  10. distillationwas distilled on a Buchi Kugelrohr apparatus (170° C./0.5 mm)

Sources & evidence

ORD record
ord-829005b5603549d5afb84f83cdc91a5a
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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