Benzhydrylamine → HCID 22110998, compound

HRID 565654Notes

Reaction equation

HRID 565654 reaction equation
[C:1]1([CH:7]([NH2:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([O:17][C:18]([N:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)=[O:19])[CH3:16]>C1(C)C=CC=CC=1>[C:1]1([CH:7]([NH:14][CH:23]2[CH2:24][CH2:25][N:20]([C:18]([O:17][CH2:15][CH3:16])=[O:19])[CH2:21][CH2:22]2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7036BenzhydrylamineHCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

Product 1

HCID 22110998HCID 22110998, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a reactor fitted with a water trap, a solution of 1,1-diphenylmethylamine (5.0 g) and 1-ethoxycarbonyl-4-piperidone (4.7 g) in toluene (70 mL) was refluxed for 4 hours. This reaction mixture was concentrated under reduced pressure and he residue was dissolved in 50 mL of ethanol. After the solution was cooled with ice, 2.1 g of sodium cyanoborohydride and a small amount of bromocresol green were added. Then, 4N-HCl solution in methanol was added dropwise until the reaction mixture had turned yellow and the mixture was further stirred for 20 minutes. This reaction mixture was poured into an access of aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1 to 65:35) to provide 8.4 g of the title compound. Yield 91%.

Workup

  1. customIn a reactor fitted with a water trap
  2. concentrationThis reaction mixture was concentrated under reduced pressure and he residue
  3. dissolutionwas dissolved in 50 mL of ethanol
  4. temperatureAfter the solution was cooled with ice, 2.1 g of sodium cyanoborohydride
  5. additiona small amount of bromocresol green were added
  6. additionThen, 4N-HCl solution in methanol was added dropwise until the reaction mixture
  7. additionThis reaction mixture was poured into an access of aqueous sodium hydrogen carbonate
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with saturated aqueous NaCl
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1 to 65:35)

Sources & evidence

ORD record
ord-2d4fc4aa9cb3494681b7a20f157a4291
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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