Hydrochloric Acid → HCID 86671368, compound

HRID 2039651Notes

Reaction equation

HRID 2039651 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][NH2:22].Cl>CO>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][C:11](=[N:22][NH:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 786452-HydrazinopyridineHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

Product 1

HCID 86671368HCID 86671368, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The following are charged to a round-bottomed flask with a magnetic stirrer: 5 g of N-Boc-piperidone, 2.45 g of pyridin-2-ylhydrazine, 100 ml of methanol and 95 ml of a solution of methanol saturated with HCl. The mixture is left to react under a nitrogen stream for 2 h at reflux temperature. The solvent is evaporated off under vacuum, the resulting product is dissolved with dichloromethane and washing is carried out with a saturated aqueous solution of NaHCO3. The organic phase is dried over Na2SO4 and the solvent is evaporated off, and 4.0 g of the title product are isolated in the form of a red oil.

Workup

  1. additionThe following are charged to a round-bottomed flask with a magnetic stirrer
  2. waitThe mixture is left
  3. customto react under a nitrogen stream for 2 h
  4. temperatureat reflux temperature
  5. customThe solvent is evaporated off under vacuum
  6. dissolutionthe resulting product is dissolved with dichloromethane
  7. washwashing
  8. dry with materialThe organic phase is dried over Na2SO4
  9. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-2ff20f6d7f1a407bb9db91eea9e6ec2d
Source dataset
uspto-grants-2013_11
Patent number
US08580790B2

Reaction notes

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