Ammonia → HCID 131723349, compound

HRID 2188399Notes

Reaction equation

HRID 2188399 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:17]([CH3:19])[CH3:18])[CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])=[CH:5][CH:4]=1.N.[CH2:21]([Mg][Cl:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>O1CCCC1.O>[ClH:29].[CH2:21]([C:11]1([OH:16])[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[CH:9]([C:6]1[CH:5]=[CH:4][C:3]([Br:2])=[CH:8][CH:7]=1)[N:17]([CH3:19])[CH3:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 69942644HCID 69942644, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 131723349HCID 131723349, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The base was freed from the 2.0 g (5.77 mmole) of the hydrochloride of 2-[(4-bromophenyl)dimethylaminomethyl]cyclohexanone obtained according to stage 1 with 20 ml of water and 5 ml of ammonia solution (25 vol. %), extracted three times with 20 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). 1.70 g (5.5 mmole) of this base were dissolved in 8.5 ml of tetrahydrofuran, added dropwise while cooling in an ice bath to 3.3 ml (6.6 mmole) of benzylmagnesium chloride (2 M solution in tetrahydrofuran), 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 10 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). 1.91 g of crude base (86.64% of theory) were obtained, from which 0.86 g of 1-benzyl-2-[(4-bromophenyl) dimethylaminomethyl]cyclohexanol, hydrochloride (35.9% of theory) were obtained according to the procedure described in Example 1 (3rd Stage) with chloro-trimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 151° C.

Workup

  1. customobtained
  2. extractionextracted three times with 20 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 10 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-d6ece4b9a7fa458887fb13a45c8af9bc
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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