Ammonia → HCID 131723359, compound

HRID 2188413Notes

Reaction equation

HRID 2188413 reaction equation
[ClH:1].[C:2]1([CH:8]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N.[Cl-].[Cl-].[NH4+]>O1CCCC1.O>[ClH:1].[CH2:8]([C:10]1([OH:15])[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[CH:8]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 312ChlorideHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 3832074HCID 3832074, compound

Product 1

HCID 131723359HCID 131723359, compoundYield 35.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The base was freed from 2.5 g (8.12 mmole) of the hydrochloride of 2-(phenylpiperidin-1-ylmethyl)cyclohexanone obtained according to stage 1 with 25 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). 2.00 g (7.4 mmole) of this base were dissolved in 10 ml of tetrahydrofuran, added dropwise to 4.4 ml (8.8 mmole) of benzylmagnesiun chloride (2 M solution in tetrahydrofuran) while cooling in an ice bath, 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 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 on a rotary evaporator (500 to 10 mbar). 2.29 g of crude base (85.4% of theory) were obtained, from which 1.05 g of 1-benzyl-2-(phenylpiperidin-1-ylmethyl)cyclohexanol, hydrochloride (35.7% of theory) was obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 218° 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 on a rotary evaporator (500 to 10 mbar)

Sources & evidence

ORD record
ord-5111b6f95c8349399e7a67e70cc1a875
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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