Ammonium Chloride → HCID 10157071, compound

HRID 2244484Notes

Reaction equation

HRID 2244484 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[Cl-].[NH4+]>O1CCCC1.C([Mg]Cl)CC1C=CC=CC=1>[CH3:18][N:2]([CH3:1])[C:3]1([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:8][CH2:7][C:6]([CH2:11][CH2:10][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)([OH:9])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 66986338HCID 66986338, compound

Product 1

HCID 10157071HCID 10157071, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418865HCID 178418865, compoundSolvent

Procedure

7.58 g 4-dimethylamino-4-phenethylcyclohexanone were dissolved in 45 ml analytical grade tetrahydrofuran, 43 ml 1.0 molar phenethylmagnesium chloride solution in THF were added under a nitrogen atmosphere, while cooling in an ice-bath, and the mixture was stirred overnight at room temperature. For working up, 43 ml ammonium chloride solution (20 per cent by weight) were added, while cooling with ice, and the mixture was extracted three times with 80 ml diethyl ether each time, the combined organic phases were extracted three times with 70 ml dilute hydrochloric acid (5 per cent by weight) each time, the combined aqueous extracts were washed with 50 ml diethyl ether, adjusted to pH 9 with ammonia solution (25 per cent by weight) and extracted three times with 80 ml methylene chloride each time, the combined methylene chloride extracts were dried over sodium sulfate, filtered and concentrated and the residue was largely freed from solvent residues in vacuo. The crude product obtained (9.57 g) was chromatographed over silica gel with diethyl ether/hexane (v/v=1:1). 938 mg of the nonpolar diastereoisomer of 4-dimethylamino-1,4-diphenethylcyclohexanol obtained were dissolved in 7.5 ml 2-butanone, 26 μl water followed by 371 μl trimethylchlorosilane were added at room temperature and the mixture was stirred overnight at room temperature. The white solid which had precipitated out was filtered with suction, washed with diethyl ether and dried in an oil pump vacuum. 1.00 g of the hydrochloride of the nonpolar diastereoisomer of 4-dimethylamino-1,4-diphenethylcyclohexanol were obtained.

Workup

  1. additionwere added under a nitrogen atmosphere
  2. temperaturewhile cooling in an ice-bath
  3. temperaturewhile cooling with ice
  4. extractionthe mixture was extracted three times with 80 ml diethyl ether each time
  5. extractionthe combined organic phases were extracted three times with 70 ml dilute hydrochloric acid (5 per cent by weight) each time
  6. washthe combined aqueous extracts were washed with 50 ml diethyl ether
  7. extractionextracted three times with 80 ml methylene chloride each time
  8. dry with materialthe combined methylene chloride extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product obtained (9.57 g)
  12. customwas chromatographed over silica gel with diethyl ether/hexane (v/v=1:1)

Sources & evidence

ORD record
ord-c0362fd609394a6bb321e5ec9e1c9a11
Source dataset
uspto-grants-2010_03
Patent number
US07678834B2

Reaction notes

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