Hydrochloric Acid → HCID 22485795, compound

HRID 2181264Notes

Reaction equation

HRID 2181264 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:17][CH2:16][C:8]2(OCC(C)(C)C[O:9]2)[CH2:7][C:6]1([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)O)[CH3:3].[ClH:27].O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[ClH:27].[CH3:3][N:2]([CH2:4][CH:5]1[CH2:17][CH2:16][C:8](=[O:9])[CH:7]=[C:6]1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15344752HCID 15344752, compound

Product 1

HCID 22485795HCID 22485795, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

182 g 9-dimethylaminomethyl-8-(3-methoxy-phenyl)-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-8-ol were dissolved in 1,200 ml tetrahydrofuran and the reaction mixture was cooled to 5° C. A mixture of 600 ml 32% hydrochloric acid solution and 600 ml water was added at this temperature. The mixture was stirred at room temperature for 72 hours. When the reaction had ended 500 ml ethyl acetate were added at 5° C. and the reaction mixture was then brought to pH 12 with 32% sodium hydroxide solution. The phases were separated and the aqueous phase was washed three times with 300 ml ethyl acetate each time. The combined organic phases were then washed twice with 100 ml saturated sodium chloride solution each time, dried over magnesium sulfate and then freed from the solvent. Purification was carried out via hydrochloride formation. For this, 4-dimethylaminomethyl-3-(3-methoxy-phenyl)-cyclohex-2-enone base was dissolved in 500 ml acetone and an equimolar amount of water and trimethylchlorosilane was added. The hydrochloride which had precipitated out was filtered off with suction and dried in vacuo. 63.6 g (78.9% of theory) 4-dimethylaminomethyl-3-(3-methoxy-phenyl)-cyclohex-2-enone hydrochloride were obtained in this way. b) rac-cis-[4-Dimethylaminomethyl-3-hydroxy-3-(3-methoxy-phenyl)-cyclohexanone]hydrochloride (compound 1)

Workup

  1. additionwas added at this temperature
  2. additionwere added at 5° C.
  3. customThe phases were separated
  4. washthe aqueous phase was washed three times with 300 ml ethyl acetate each time
  5. washThe combined organic phases were then washed twice with 100 ml saturated sodium chloride solution each time
  6. dry with materialdried over magnesium sulfate
  7. customPurification
  8. dissolutionFor this, 4-dimethylaminomethyl-3-(3-methoxy-phenyl)-cyclohex-2-enone base was dissolved in 500 ml acetone
  9. additionan equimolar amount of water and trimethylchlorosilane was added
  10. customThe hydrochloride which had precipitated out
  11. filtrationwas filtered off with suction
  12. customdried in vacuo

Sources & evidence

ORD record
ord-941fb7553f164ae08ea8c694888a9374
Source dataset
uspto-grants-2005_05
Patent number
US06890959B2

Reaction notes

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