Ammonium Chloride → HCID 131723354, compound

HRID 2188404Notes

Reaction equation

HRID 2188404 reaction equation
[CH3:1][N:2]([CH:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])[CH3:3].[CH2:19]([Mg][Cl:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1>[ClH:27].[CH2:19]([C:6]1([OH:11])[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]1[CH:4]([N:2]([CH3:1])[CH3:3])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 22447884HCID 22447884, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 131723354HCID 131723354, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (7.5 mmole) of the 2-(dimethylamino-o-tolylmethyl) cyclohexanone prepared according to Example 66 were dissolved in 15 ml of tetrahydrofuran, added dropwise while cooling in an ice bath to 6.1 ml (12.2 mmole) of benzylmagnesium chloride (2 M solution in tetrahydrofuran), and stirred for 15 hours at RT. The reaction mixture was worked up by adding 158 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). 3.39 g of crude base (98.5% of theory) were obtained, from which 0.83 g of 1-benzyl-2-(dimethylamino-o-tolylmethyl)cyclo-hexanol, hydrochloride (21.8% of theory) having a melting point of 180-183° C. was obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone.

Workup

  1. additionadded dropwise
  2. temperaturewhile cooling in an ice bath
  3. extractionwas extracted three times at RT with 15 ml of ether each time
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)

Sources & evidence

ORD record
ord-1c3792fd481e4e06a8541e2929219984
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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