Ammonium Chloride → HCID 131723348, compound

HRID 2188395Notes

Reaction equation

HRID 2188395 reaction equation
[Mg].[F:2][C:3]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Br.[CH3:12][N:13]([CH:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=[O:22])[CH3:14].[Cl-:29].[NH4+]>CCOCC>[ClH:29].[F:2][C:3]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][C:17]1([OH:22])[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[CH:15]([N:13]([CH3:12])[CH3:14])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 5462224MagnesiumHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanone

Product 1

HCID 131723348HCID 131723348, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

0.41 g (16.8 mmole) of magnesium turnings was stirred in 10 ml of ether of analysis purity. 3.47 g (16.8 mmole) of 2,3-difluorobenzyl 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. 3.23 g (14.0 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 20 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT with 20 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). 5.13 g of crude base (102% of theory) were obtained, from which 1.67 g of 1-(2,3-difluorobenzyl)-2-(dimethylamino-phenylmethyl)cyclohexanol, hydrochloride (30.0% 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 140° 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 20 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-4f6064702bd346c397d7f13bbc4ca1c7
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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