Ammonia → HCID 131723357, compound

HRID 2188411Notes

Reaction equation

HRID 2188411 reaction equation
Cl.[CH3:2][N:3]([CH:5]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])[CH3:4].N.[CH2:24]([Mg][Cl:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-].[NH4+]>O1CCCC1.O>[ClH:32].[CH2:24]([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[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 69942253HCID 69942253, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 131723357HCID 131723357, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The base was freed from 3.0 g (9.44 mmole) of the hydrochloride of 2-(dimethylaminonaphthalene-2-ylmethyl)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 one a rotary evaporator without heating (500 to 10 mbar). 2.5 g (8.9 mmole) of this base were dissolved in 15 ml of tetrahydrofuran, added dropwise while cooling in an ice bath to 5.3 ml (10.7 mmole) of benzylmagnesium 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 20 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT with 20 ml. of other each time. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 3.17 g of crude base (99.2% of theory) were obtained, from which 2.4 g of 1-benzyl-2-(dimethylaminonaphthalene-2-yl-methyl)cyclohexanol, hydrochloride (68.1% 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 180° 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 one
  6. customa rotary evaporator
  7. temperaturewithout heating (500 to 10 mbar)
  8. additionadded dropwise
  9. temperaturewhile cooling in an ice bath
  10. extractionwas extracted three times at RT with 20 ml
  11. dry with materialThe combined organic extracts were dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)

Sources & evidence

ORD record
ord-a4265659b9f14741a5df5cca53483d61
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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