Ammonium Chloride → 2-[(3,4-Dichlorophenyl)dimethylaminomethyl]-1-phenethylcyclo-hexanol, hydrochloride

HRID 2188382Notes

Reaction equation

HRID 2188382 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:17]([CH3:19])[CH3:18])[CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:20]([Mg]Cl)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+].Cl[Si](C)(C)C.O>O1CCCC1.CC(=O)CC.CCCCCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:17]([CH3:19])[CH3:18])[CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[OH:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 699429172-[(3,4-Dichlorophenyl)dimethylaminomethyl]cyclohexanoneHCID 86753056Chlorotrimethylsilane waterHCID 178418865HCID 178418865, compound

Product 1

HCID 1317233362-[(3,4-Dichlorophenyl)dimethylaminomethyl]-1-phenethylcyclo-hexanol, hydrochlorideYield 137.3%

Reagents, catalysts & solvents 3

HCID 6569Methyl Ethyl KetoneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

3.0 g (10.0 mmole) of the 2-[(3,4-dichlorophenyl)dimethylaminomethyl]cyclohexanone prepared according to Example 39 were dissolved in 10 ml of tetrahydrofuran, added dropwise while cooling in an ice bath to 12.0 ml (12.0 mmole) of phenethylmagnesium chloride (1 M solution in tetrahydrofuran) and stirred for 15 hours at RT. The reaction solution 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 in each case 15 ml of ether. The combined organic extracts were dried over sodium sulfate, filtered and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 3.88 g of crude base (95.5% of theory) were obtained from which, after adding 30 ml of n-hexane, an oil was obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/ water in 2-butanone. After decanting the solvents the oil was stirred in 5 ml of water and 20 ml of ether, arid the resultant precipitate was filtered off and dried. 3.04 g of 2-[(3,4-dichlorophenyl)dimethylaminomethyl]-1-phenethylcyclo-hexanol, hydrochloride (68.7% of theory) were obtained in this way. The hydrochloride decomposes on heating above 130° C.

Workup

  1. additionadded dropwise
  2. temperaturewhile cooling in an ice bath
  3. extractionwas extracted three times at RT with in each case 15 ml of ether
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)
  7. custom3.88 g of crude base (95.5% of theory) were obtained from which
  8. customan oil was obtained
  9. customAfter decanting the solvents the oil
  10. stirringwas stirred in 5 ml of water
  11. filtrationwas filtered off
  12. customdried

Sources & evidence

ORD record
ord-b7fe3fad177b43bf8a9cfd81fb5951d7
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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