Ammonia → HCID 131723340, compound

HRID 2188385Notes

Reaction equation

HRID 2188385 reaction equation
Cl.[Cl:2]C1C=C([C:9]2([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[OH:15])C=CC=1.[Cl:26][C:27]1[CH:28]=[C:29](C2(CN(C)C)CCCCC2=O)[CH:30]=[CH:31][CH:32]=1.N.C1([Mg]Cl)C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1.O>[ClH:2].[Cl:26][C:27]1[CH:32]=[C:31]([CH:22]([N:23]([CH3:24])[CH3:25])[CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[OH:15])[CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 131723338HCID 131723338, compoundHCID 131723341HCID 131723341, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 131723340HCID 131723340, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The base was freed from 2.5 g (8.27 mmole) of the hydrochloride of 2-[(3-chlorophenyl)(dimethylaminomethyl]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). 2.0 g (7.5 mmole) of this base were dissolved in 5 ml of tetrahydrofuran, added dropwise while cooling in an ice bath to 4.5 ml (9.0 mmole) of phenylmagnesium chloride (2 M solution in tetrahydro-furan), and the whole was 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). 2.30 g of crude base (88.8% of theory) were obtained, from which 2.18 g of 2-[(3-chlorophenyl)dimethylaminomethyl]-1-phenylcyclohexanol, hydrochloride (76.2% 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 139° 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 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-dab4466d5bc54233990c17ff4aa9b8b4
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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