Ammonium Chloride → HCID 131723346, compound

HRID 2188392Notes

Reaction equation

HRID 2188392 reaction equation
[CH3:1][N:2]([CH:4]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=1)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])[CH3:3].[CH2:25]([Mg][Cl:34])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Cl-].[NH4+]>O1CCCC1>[ClH:34].[CH3:3][N:2]([CH:4]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:13]=1)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[OH:11])[CH3:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 22447830HCID 22447830, compoundHCID 178418865HCID 178418865, compound

Product 1

HCID 131723346HCID 131723346, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (6.2 mmole) of the 2-[dimethylamino-(3-phenoxy-phenyl)methyl]cyclohexanone prepared according to Example 34 were dissolved in 9 ml of tetrahydrofuran, added dropwise while cooling in an ice bath to 7.4 ml (9.0 mmole) of phenethylmagnesium chloride (1 M solution in tetrahydrofuran), and stirred for 15 hours at RT. The reaction mixture was worked up by adding 10 ml of saturated ammonium chloride solution while cooling in an ice bath, and extracted three times at RT with 10 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). 2.55 g of crude base (96.0% of theory) were obtained, from which a hydrochloride was precipitated according to Example 1 (3rd stage) with chlorotrimethylsilane/water in 2-butanone. The base was freed from the hydrochloride with 20 ml of water and 5 ml of ammonia solution (25 vol. %), extracted three times, each time with 10 ml of ether, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 1.51 g of crude base (56.8% of theory) were obtained, from which 1.31 g of 2-[dimethylamino-(3-phenoxyphenyl)methyl]-1-phenethylcyclohexanol, hydrochloride (45.2% 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 120° C.

Workup

  1. additionadded dropwise
  2. temperaturewhile cooling in an ice bath
  3. extractionextracted three times at RT with 10 ml of ether each time
  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. custom2.55 g of crude base (96.0% of theory) were obtained, from which a hydrochloride
  8. customwas precipitated
  9. extractionextracted three times
  10. dry with materialeach time with 10 ml of ether, and the combined organic extracts were dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)

Sources & evidence

ORD record
ord-fb5e21bc84aa4c29be7cde14e91add97
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

Loading…