Ammonium Chloride → 2-(Dimethylaminophenyl-methyl)-1-(2-methylsulfanylphenyl)cyclohexanol, hydrochloride

HRID 2188410Notes

Reaction equation

HRID 2188410 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1I.C([Mg][Cl:14])(C)C.[CH3:15][N:16]([CH:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1=[O:25])[CH3:17].[Cl-].[NH4+]>CCOCC>[ClH:14].[CH3:17][N:16]([CH:18]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[S:2][CH3:1])[OH:25])[CH3:15]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 28014161-Iodo-2-methylsulfanylbenzeneHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanoneHCID 178418918HCID 178418918, compound

Product 1

HCID 1317233562-(Dimethylaminophenyl-methyl)-1-(2-methylsulfanylphenyl)cyclohexanol, hydrochlorideYield 57%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-10 °C

Procedure

0.811 g (3.24 mmole) of 2-methylmercaptoiodobenzene were dissolved in 2 ml of ether, cooled to −10° C., and 1.62 ml (3.24 mmole) of isopropylmagnesium chloride (2 M solution in tetrahydrofuran) were added dropwise. After stirring for one hour at ° C., 0.50 g (2.16 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 and dissolved in 2 ml of ether was added dropwise, and the whole was stirred for 15 hours at RT. The reaction mixture was worked up by adding 2 ml of saturated ammonium chloride solution while cooling in an ice bath and was extracted three times at RT with 5 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). 0.84 g of crude base (109% of theory) was obtained, from which 0.483 g of 2-(dimethylaminophenyl-methyl)-1-(2-methylsulfanylphenyl)cyclohexanol, hydrochloride (38.0% of theory) was obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 230° C.

Workup

  1. additionwas added dropwise
  2. stirringthe whole was stirred for 15 hours at RT
  3. temperaturewhile cooling in an ice bath
  4. extractionwas extracted three times at RT with 5 ml of ether each time
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)

Sources & evidence

ORD record
ord-4c047f09fe604086bae45519c6009206
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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