Hydrochloric Acid → HCID 18753166, compound

HRID 1838118Notes

Reaction equation

HRID 1838118 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6](/[CH:10]=[C:11]2\[CH:12]=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[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:28])=[O:2])/[CH:12]=[C:13]1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1)[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59059229HCID 59059229, compound

Product 1

HCID 18753166HCID 18753166, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

3 g of the Z-3-[4-Dimethylaminomethyl-3-(3-hydroxy-phenyl)-cyclohex-2-enylidenmethyl]-benzoic acid methyl ester, as the base, prepared according to example 32 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. Z-3-[4-Dimethylaminomethyl-3-(3-hydroxy-phenyl)-cyclohex-2-enylidenmethyl]-benzoic acid, 2.7 g in the form of an orange-yellow oil, was obtained in this way. 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 (77.7% of theory) Z-3-[4-dimethylaminomethyl-3-(3-hydroxy-phenyl)-cyclohex-2-enylidenmethyl]-benzoic acid hydrochloride were obtained in this way.

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-0082fb5417274e07a52c9e1d85168371
Source dataset
uspto-grants-2004_01
Patent number
US06673794B2

Reaction notes

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