Hydrochloric Acid → 2-benzylidene-6-dimethylaminomethyl-cyclohexanone

HRID 2414768Notes

Reaction equation

HRID 2414768 reaction equation
[CH:1](=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.[CH3:18][NH2+:19][CH3:20].[C:21](Cl)(=O)C.Cl.ClCCl.[OH-].[Na+]>C(#N)C.CCOCC>[CH:1](=[C:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:18][N:19]([CH3:21])[CH3:20])[C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 6367Acetyl chlorideHCID 989262-BenzylidenecyclohexanoneHCID 22610303HCID 22610303, compoundHCID 23721229Sodium hydroxide methylene chloride

Product 1

HCID 3822752-benzylidene-6-dimethylaminomethyl-cyclohexanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

43 g (0.23 mole) of 2-benzylidene-cyclohexanone obtained from Stage 2, and 21.6 g (0.23 mole) of dimethylammonium methylene chloride were stirred in 200 ml of dry acetonitrile at room temperature. After adding 0.2 ml of acetyl chloride the reaction mixture was stirred for a further 3 hours at room temperature, a colorless clear solution being formed. 200 ml of dry ether were then added dropwise to the reaction mixture, whereupon the hydrochloride crystallized out. 56.1 g (87% of theory) of colorless crystals were obtained. The base was released from the hydrochloride with dichloromethane/sodium hydroxide and, after drying the solution, the dichloromethane was removed by distillation.

Workup

  1. customa colorless clear solution being formed
  2. customcrystallized out
  3. custom56.1 g (87% of theory) of colorless crystals were obtained
  4. customafter drying the solution
  5. customthe dichloromethane was removed by distillation

Sources & evidence

ORD record
ord-98315c2e82da42ce97d8e67e29e48686
Source dataset
uspto-grants-2004_11
Patent number
US06815443B2

Reaction notes

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