Ammonium Chloride → HCID 131723331, compound

HRID 2188373Notes

Reaction equation

HRID 2188373 reaction equation
[Mg].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br.[CH3:12][N:13]([CH3:32])[CH:14]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=[O:21].[Cl-:33].[NH4+]>CCOCC>[ClH:33].[CH3:32][N:13]([CH:14]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][CH:23]=1)[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1([CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([O:3][CH3:2])[CH:5]=1)[OH:21])[CH3:12]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 40672073-Methoxybenzyl bromideHCID 5462224MagnesiumHCID 22447855HCID 22447855, compound

Product 1

HCID 131723331HCID 131723331, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

0.29 g (12.0 mmole) of magnesium turnings was stirred in 5 ml of ether of analysis purity. 2.42 g (12.0 mmole) of 3-methoxybenzyl bromide dissolved in 10 ml of ether were added dropwise so that the reaction mixture boiled gently. After completion of the addition the reaction mixture was stirred for a further hour at RT. 3.0 g (10.0 mmole) of the 2-[dimethyl-amino-(4-trifluoromethylphenyl)methyl]cyclohexanone prepared according to stage 2 were dissolved in 5 ml of ether, 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 ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT, each time with 50 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). 5.60 g of crude base (133% of theory) were obtained. 3.26 g of 2-[dimethylamino-(4-trifluoromethyl-phenyl)methyl]-1-(3-methoxybenzyl)cyclohexanol, hydrochloride (70.9% of theory) were obtained from the crude base according to the procedure described in Example 1 (3rd stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 133° C.

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
  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. custom5.60 g of crude base (133% of theory) were obtained

Sources & evidence

ORD record
ord-0b090955a30346fa88a9a4135eb17f51
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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