Chloride → HCID 22447911, compound

HRID 2188375Notes

Reaction equation

HRID 2188375 reaction equation
[Mg].Br[C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[O:11][CH3:12].[CH3:13][N:14]([CH:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=[O:23])[CH3:15].[Cl-:30]>O1CCCC1>[ClH:30].[CH3:12][O:11][C:4]1[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[C:18]1([OH:23])[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[CH:16]([N:14]([CH3:13])[CH3:15])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 91353Benzene, 2-bromo-1,4-dimethoxy-HCID 5462224MagnesiumHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanone

Product 1

HCID 22447911HCID 22447911, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
65 °C

Procedure

0.38 g (15.6 mmole) of magnesium turnings was stirred in 15 ml of tetrahydrofuran of analysis purity. 3.39 g (15.6 mmole) of 1-bromo-2,5-dimethoxybenzene dissolved in 15 ml of tetrahydrofuran were added dropwise so that the reaction mixture boiled gently. After completion of the addition the reaction mixture was stirred for a further 1.5 hours at 65° C. 3.0 g (13.0 mmole) of the 2-(dimethylaminophenylmethyl) cyclohexanone prepared according to Example 1 were dissolved in 15 ml of tetrahydro-furan, added dropwise to the Grignard reagent while cooling in an ice bath, and stirred for 15 hours at RT. The reaction solution was worked up by adding 30 ml of saturated anmonium chloride solution while cooling in an ice bath, and was extracted three times at RT with in each case 60 ml of ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 5.17 g of crude base (108% of theory) were obtained. 4.43 g of 1-(2,5-dimethoxy-phenyl)-2-(dimethylaminophenylmethyl)cyclohexanol, hydrochloride (84.2% of theory) with a melting point above 240° C. were obtained from the crude base according to the procedure described in Example 1 (3rd stage) with chlorotri-methylsilane/water in 2-butanone.

Workup

  1. additionwere added dropwise so that the reaction mixture
  2. additionAfter completion of the addition the reaction mixture
  3. temperaturewhile cooling in an ice bath
  4. stirringstirred for 15 hours at RT
  5. temperaturewhile cooling in an ice bath
  6. extractionwas extracted three times at RT with in each case 60 ml of ethyl acetate
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)
  10. custom5.17 g of crude base (108% of theory) were obtained

Sources & evidence

ORD record
ord-45a2a446b0f743bc95badbe563c7b806
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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