Sodium Hydroxide → HCID 69338491, compound

HRID 1179039Notes

Reaction equation

HRID 1179039 reaction equation
[CH2:1]([C:8]1([N:15]([CH3:17])[CH3:16])[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:19][NH2:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O1CCCC1.C(O)(=O)C.C(N(CC)CC)C>[CH2:1]([C:8]1([N:15]([CH3:17])[CH3:16])[CH2:13][CH2:12][CH:11]([NH:20][CH3:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochlorideHCID 204534784-Benzyl-4-(dimethylamino)cyclohexanone

Product 1

HCID 69338491HCID 69338491, compoundYield 41.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

15.0 g 4-benzyl-4-dimethylamino-cyclohexanone (see example 3) were dissolved in 225 ml analytical grade tetrahydrofuran, and 4.38 g methylamine hydrochloride, 8.9 ml triethylamine and 8.40 ml glacial acetic acid were added, while stirring in an ice-bath. 19.2 g sodium triacetoxyborohydride were then added in portions in the course of 15 minutes and the mixture was subsequently stirred overnight. For working up, 110 ml two molar sodium hydroxide solution were added dropwise (pH>10) and the mixture was extracted three times with 200 ml diethyl ether each time. The combined organic phases were washed twice with 200 ml water each time, dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product obtained (15.0 g) was chromatographed over silica gel with methanol with the addition of one percent by volume of aqueous ammonia solution (25 wt. %). 11.6 g of the still significantly contaminated product were obtained, and were chromatographed again over silica gel with ethyl acetate and an addition of methanol rising from twenty-five to fifty percent by volume. 6.67 g 1-benzyl-N,N,N′-trimethyl-cyclohexane-1,4-diamine were obtained as a cis/trans mixture.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted three times with 200 ml diethyl ether each time
  3. washThe combined organic phases were washed twice with 200 ml water each time
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product obtained (15.0 g)
  8. customwas chromatographed over silica gel with methanol with the addition of one percent by volume of aqueous ammonia solution (25 wt. %)
  9. custom11.6 g of the still significantly contaminated product were obtained
  10. customwere chromatographed again over silica gel with ethyl acetate
  11. additionan addition of methanol rising from twenty-five to fifty percent by volume

Sources & evidence

ORD record
ord-15e00fb37cef455a9001187c1f30c07f
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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