Benzylamine → HCID 9922658, compound

HRID 1179030Notes

Reaction equation

HRID 1179030 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O1CCCC1.C(O)(=O)C>[CH2:17]([NH:24][CH:6]1[CH2:7][CH2:8][C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([N:2]([CH3:16])[CH3:1])[CH2:4][CH2:5]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 9922658HCID 9922658, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.00 g 4-dimethylamino-4-phenyl-cyclohexanone were dissolved in 30 ml analytical grade tetrahydrofuran, and 986 mg benzylamine followed by 794 μl glacial acetic acid were added, while stirring in an ice-bath. 2.72 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. %). 844 mg of the nonpolar diastereoisomer of N′-benzyl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained, and were converted into 843 mg of the corresponding hydrochloride by dissolving in 6.8 ml 2-butanone and addition of 27.1 μl water followed by 381 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-eb1db1b910974923ae7729fd0ad75fbe
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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