Hydrochloric Acid → HCID 15541115, compound

HRID 1838113Notes

Reaction equation

HRID 1838113 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6](/[CH:10]=[C:11]2\[C:12](C)=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)[CH:14]([CH2:17][N:18]([CH3:20])[CH3:19])[CH2:15][CH2:16]\2)[CH:5]=1.[OH-].[K+].Cl>CO>[CH3:19][N:18]([CH2:17][CH:14]1[CH2:15][CH2:16]/[C:11](=[CH:10]/[C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:30])=[O:2])/[CH:12]=[C:13]1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69862939HCID 69862939, compound

Product 1

HCID 15541115HCID 15541115, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

3 g of the Z-3-[4-dimethylaminomethyl-3-(3-methoxy-phenyl)-2-methyl-cyclohex-2-enylidenemethyl]-benzoic acid methyl ester, as the base, prepared according to example 1 were dissolved in 30 ml methanol, and 30 ml 1 N potassium hydroxide solution were added. The mixture was stirred at 60° C. for 2 hours. After the reaction mixture had cooled to room temperature, 1 N hydrochloric acid was added to the mixture until a pH of 4 was established. The phases were separated and the aqueous phase was washed 3 times with 20 ml ethyl acetate each time. The combined organic phases were dried over magnesium sulfate and freed from the solvent in vacuo. 2.7 g Z-3-[4-dimethylaminomethyl-3-(3-methoxy-phenyl)-cyclohex-2-enylidenemethyl]-benzoic acid base were obtained in this way in the form of an orange-yellow oil. To prepare the hydrochloride, the base was dissolved in 10 ml acetone, and an equimolar amount of trimethylchlorosilane and water was added. 2.4 g (77% of theory) Z-3-[4-dimethylaminomethyl-3-(3-methoxy-phenyl)-cyclohex-2-enylidenemethyl]-benzoic acid hydrochloride (14) were obtained in this way in the form of white crystals.

Workup

  1. temperatureAfter the reaction mixture had cooled to room temperature
  2. customThe phases were separated
  3. washthe aqueous phase was washed 3 times with 20 ml ethyl acetate each time
  4. dry with materialThe combined organic phases were dried over magnesium sulfate

Sources & evidence

ORD record
ord-e0122c5b4a364fa8a2b830e13ecd07eb
Source dataset
uspto-grants-2004_01
Patent number
US06673794B2

Reaction notes

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