Ammonium Chloride → (1-Benzyl-4-benzyloxycyclo-hexyl)dimethylamine

HRID 1349384Notes

Reaction equation

HRID 1349384 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([N:17]([CH3:19])[CH3:18])([C:15]#N)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:15]([C:12]1([N:17]([CH3:19])[CH3:18])[CH2:13][CH2:14][CH:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH2:11]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 210932404-Benzyloxy-1-dimethylaminocyclohexanecarbonitrileHCID 178418336HCID 178418336, compound

Product 1

HCID 10125753(1-Benzyl-4-benzyloxycyclo-hexyl)dimethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.00 g of 4-benzyloxy-1-dimethylaminocyclohexanecarbonitrile were dissolved in 40 ml of tetrahydrofuran, and 10.8 ml of two molar benzylmagnesium chloride solution in tetrahydrofuran were added dropwise under a nitrogen atmosphere, while cooling with an ice bath. After stirring overnight at room temperature, the mixture was again cooled in an ice bath, and 20 ml of cold ammonium chloride solution (20 percent by weight) were added. The phases were separated and extracted twice using 60 ml of diethyl ether each time, the combined organic phases were extracted three times using 50 ml of hydrochloric acid (5 percent by weight) each time, the combined acidic extracts were rendered weakly alkaline (pH 8–9) with aqueous ammonia solution (25 percent by weight) and extracted three times using 60 ml of diethyl ether each time, and the combined organic extracts were dried over sodium sulfate, filtered and concentrated. The resulting yellow solid (3.85 g) was separated on silica gel with diethyl ether/hexane (V:V=1:1). 2.45 g of (1-benzyl-4-benzyloxycyclo-hexyl)dimethylamine were obtained in the form of a white solid which, as described for Example 1, was converted into 2.03 g of the corresponding hydrochloride (white solid) using chlorotrimethylsilane and water in 2-butanone.

Workup

  1. temperaturewhile cooling with an ice bath
  2. temperaturethe mixture was again cooled in an ice bath
  3. customThe phases were separated
  4. extractionextracted twice
  5. extractionthe combined organic phases were extracted three times
  6. extractionextracted three times
  7. dry with materialthe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting yellow solid (3.85 g) was separated on silica gel with diethyl ether/hexane (V:V=1:1)

Sources & evidence

ORD record
ord-5397156d8950404fa88a5dfc32980225
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

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