Diethyl Ether → HCID 131723343, compound

HRID 2188388Notes

Reaction equation

HRID 2188388 reaction equation
[Mg].[Cl:2][C:3]1[CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:7][CH:8]=1.[CH3:13][N:14]([CH:16]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=[O:23])[CH3:15].[Cl-].[NH4+].[CH3:33]COCC>>[ClH:2].[CH3:15][N:14]([CH:16]([C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1([CH2:33][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:4]=1)[OH:23])[CH3:13]

Participants

6

Reactant 5

HCID 3283Diethyl Ether3×HCID 73743-ChlorobenzotrifluorideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 22447907HCID 22447907, compound

Product 1

HCID 131723343HCID 131723343, compoundYield 69.1%

Procedure

0.29 g (12.1 mmole) of magnesium turnings was stirred in 5 ml of ether of analysis purity. 2.35 g (12.1 mmole) of 3-chlorobenzotrifluoride dissolved in 5 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. 2.51 g (10.1 mmole) of the 2-[dimethylamino-(4-fluorophenyl)methyl]cyclohexanone prepared according to Example 41 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 mixture was worked up by adding 15 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT with 15 ml of ether each time. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 4.15 g of crude base (101% of theory) were obtained, from which 3.10 g of 2-[dimethylamino-(4-fluorophenyl)methyl]-1-(3-trifluoromethylbenzyl)cyclo-hexanol, hydrochloride (69.1% of theory) were obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 210° 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 with 15 ml of ether each time
  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)

Sources & evidence

ORD record
ord-3338dafc21ac4512a1338d15985dcb1b
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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