Ethylamine → HCID 69337829, compound

HRID 1179041Notes

Reaction equation

HRID 1179041 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.[CH2:18]([NH2:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O1CCCC1.C(O)(=O)C>[CH2:1]([C:8]1([N:15]([CH3:17])[CH3:16])[CH2:13][CH2:12][CH:11]([NH:20][CH2:18][CH3:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6341EthylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 204534784-Benzyl-4-(dimethylamino)cyclohexanone

Product 1

HCID 69337829HCID 69337829, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

15.0 g 4-benzyl-4-dimethylamino-cyclohexanone (see example 3) were dissolved in 225 ml analytical grade tetrahydrofuran, and 2.89 g ethylamine followed by 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 (15.7 g) was chromatographed over silica gel with methanol with the addition of one percent by volume of aqueous ammonia solution (25 wt. %). 14.1 g of the still significantly contaminated product were obtained, and were chromatographed again over silica gel with methanol with the addition of one percent by volume of aqueous ammonia solution (25 wt. %). 12.1 g 1-benzyl-N′-ethyl-N,N-dimethyl-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 (15.7 g)
  8. customwas chromatographed over silica gel with methanol with the addition of one percent by volume of aqueous ammonia solution (25 wt. %)
  9. custom14.1 g of the still significantly contaminated product were obtained
  10. customwere chromatographed again over silica gel with methanol with the addition of one percent by volume of aqueous ammonia solution (25 wt. %)

Sources & evidence

ORD record
ord-06d676067abc40cf8b597ec90c895fc9
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

Loading…