Ammonium Chloride → HCID 131723360, compound

HRID 2188414Notes

Reaction equation

HRID 2188414 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[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].[NH4+]>CCOCC>[ClH:30].[CH3:15][N:14]([CH:16]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1([C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1)[OH:23])[CH3:13]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 5462224MagnesiumHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanone

Product 1

HCID 131723360HCID 131723360, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

0.76 g (31.0 mmole) of magnesium turnings was stirred in 15 ml. of ether of analysis purity. 4.46 ml (31.0 mmole) of 4-bromobenzotrifluoride dissolved in 15 ml of ether were arddecl dropwise so that the reaction mixture boiled gently. After completion of the addition the reaction mixture was stirred for a further hour at RT. 6.0 g (26.0 mmole) of the 2-{dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 were dissolved in 15 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 30 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT with 50 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). 8.49 g of crude base (86.7% of threory) were obtained, from which 6.62 g of 2-{dimethylaminophenylmethyl)-1-(4-trifluoromethylphenyl)cyclohexanol, hydrochloride (61.7% 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 170° C.

Workup

  1. additionAfter completion of the addition the reaction mixture
  2. temperaturewhile cooling in an ice bath
  3. stirringstirred for 15 hours at RT
  4. temperaturewhile cooling in an ice bath
  5. extractionwas extracted three times at RT with 50 ml of ether each time
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)

Sources & evidence

ORD record
ord-4627843053c74ac89b887e6cde74cc50
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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