Ammonia → HCID 131723358, compound

HRID 2188412Notes

Reaction equation

HRID 2188412 reaction equation
Cl.[CH3:2][N:3]([CH:5]([C:13]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[C:14]=1[F:23])[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])[CH3:4].N.[CH2:25]([Mg][Cl:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl-].[NH4+]>O1CCCC1.O>[ClH:33].[CH2:25]([C:7]1([OH:12])[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[CH:5]([N:3]([CH3:2])[CH3:4])[C:13]1[C:14]([F:23])=[C:15]([F:22])[C:16]([F:21])=[C:17]([F:20])[C:18]=1[F:19])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 22447843HCID 22447843, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 131723358HCID 131723358, compoundYield 19.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The base was freed from 3.0 g (8.39 mmole) of the hydrochloride of 2-(dimethylaminopentafluorophenylmethyl) 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). 2.5 g (7.8 mmole) of this base were dissolved in 12 ml of tetrahydrofuran, added dropwise to 4.7 ml (9.3 mmole) of benzylmagnesium chloride (2 M solution in tetrahydrofuran) while cooling in an ice bath, and then 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 was extracted three times at RT with 15 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). 2.46 g of crude base (76.4% of theory) were obtained, from which 0.68 g of 1-benzyl-2-(dimethylaminopentafluorophenylmethyl)cyclohexanol, hydrochloride (19.4% of theory) was obtained according to the procedure described in Example 1 (3rd Stage). The hydrochloride decomposes on heating above 100° 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. temperaturewhile cooling in an ice bath
  8. temperaturewhile cooling in an ice bath
  9. extractionwas extracted three times at RT with 15 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-9c7450755f5b4c6e8a96103a801b64d6
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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