Piperazine → HCID 57157975, compound

HRID 342497Notes

Reaction equation

HRID 342497 reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]2[C:16](=O)[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[BH3-]C#N.[Na+]>CO>[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:16]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 5003444Sodium cyanoborohydrideHCID 156391233-Benzyl-3-azabicyclo[3.3.1]nonan-9-one

Product 1

HCID 57157975HCID 57157975, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-benzyl-3-azabicyclo[3.3.1]nonan-9-one (0.72 g, 3.14 mmol), methanol (25 ml), piperazine(2.71 g, 31.4 mmol), several 3A molecular sieves, and NaBH3CN (0.39 g, 6.28 mmol) was refluxed for 60 hr, cooled, and concentrated. The residue was taken up in 1N HCl (50 ml), washed with ethyl acetate, the pH adjusted to 12 with 1N NaOH aqueous solution, and extracted with dichloromethane. The extract was dried over Na2SO4 and concentrated to afford 0.72 g (72% crude) of an oil, which was used directly in the following step.

Workup

  1. temperaturewas refluxed for 60 hr
  2. temperaturecooled
  3. concentrationconcentrated
  4. washwashed with ethyl acetate
  5. extractionextracted with dichloromethane
  6. dry with materialThe extract was dried over Na2SO4
  7. concentrationconcentrated
  8. customto afford 0.72 g (72% crude) of an oil, which

Sources & evidence

ORD record
ord-aec35423f4ba45a99abee71cf1956101
Source dataset
uspto-grants-1999_01
Patent number
US05859011

Reaction notes

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