Ammonia → HCID 131723353, compound

HRID 2188403Notes

Reaction equation

HRID 2188403 reaction equation
Cl.[CH3:2][N:3]([CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])[CH3:4].N.[C:21]1([Mg][Cl:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>O1CCCC1.O>[ClH:28].[CH3:4][N:3]([CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:12])[CH3:2]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 22447884HCID 22447884, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 131723353HCID 131723353, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The base was freed from 3.0g (10.6 mmole) of the hydrochloride of 2-(dimethylamino-o-tolylmethyl) cyclohexanone obtained according to stage 1 with 30 ml of water and 5 ml of ammonia solution (25 vol. %), extracted three times with 30 ml of ether each time, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator without heating (500 to 10 mbar). 2.50 g (10.2 mmole) of this base were dissolved in 15 ml of tetrahydrofuran, added dropwise while cooling in an ice bath to 6.1 ml (12.2 mmole) of phenylmagnesium chloride (2 M solution in tetrahydro-furan), and stirred for 15 hours at RT. The reaction mixture 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 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). 3.12 g of crude base (94.5% of theory) were obtained, from which 1.97 g of 2-(dimethylamino-o-tolylmethyl)-1-phenylcyclohexanol, hydrochloride (53.7% 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 137° C.

Workup

  1. customobtained
  2. extractionextracted three times with 30 ml of ether each time
  3. dry with materialthe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation on a rotary evaporator
  6. temperaturewithout heating (500 to 10 mbar)
  7. additionadded dropwise
  8. temperaturewhile cooling in an ice bath
  9. extractionwas extracted three times at RT with 20 ml of ether each time
  10. dry with materialThe 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-2a82ddf7b0a24eb1a505e848b708d72a
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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