Benzylamine → HCID 9858357, compound

HRID 1179033Notes

Reaction equation

HRID 1179033 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]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.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:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 204534784-Benzyl-4-(dimethylamino)cyclohexanone

Product 1

HCID 9858357HCID 9858357, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.00 g 4-benzyl-4-dimethylamino-cyclohexanone were dissolved in 30 ml analytical grade tetrahydrofuran, and 926 mg benzylamine followed by 746 μl glacial acetic acid were added, while stirring in an ice-bath. 2.56 g sodium triacetoxyborohydride were then added in portions in the course of 15 minutes and the mixture was subsequently stirred for approx. 65 hours. For working up, 15 ml two molar sodium hydroxide solution were added dropwise (pH>10) and the mixture was extracted three times with 25 ml diethyl ether each time. The combined organic phases were then washed twice with 20 ml water each time, dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product obtained was chromatographed over silica gel with diethyl ether with the addition of one percent by volume of aqueous ammonia solution (25 wt. %). 774 mg of the nonpolar diastereoisomer of 1,N′-dibenzyl-N,N-dimethyl-cyclohexane-1,4-diamine were obtained, and were converted into 731 mg of the corresponding hydrochloride by dissolving in 6.2 ml 2-butanone and addition of 23.8 μl water followed by 334 μl chlorotrimethylsilane and stirring overnight.

Workup

  1. additionwere added
  2. stirringthe mixture was subsequently stirred for approx. 65 hours
  3. extractionthe mixture was extracted three times with 25 ml diethyl ether each time
  4. washThe combined organic phases were then washed twice with 20 ml water each time
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe crude product obtained
  9. customwas chromatographed over silica gel with diethyl ether with the addition of one percent by volume of aqueous ammonia solution (25 wt. %)

Sources & evidence

ORD record
ord-acef306ea49e4197b98830199ca92776
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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