Benzoylhydrazine → N'-(1-Methylpiperidin-4-yl)benzohydrazide

HRID 1905018Notes

Reaction equation

HRID 1905018 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.[BH4-].[Na+]>CO>[C:1]([NH:9][NH:10][CH:15]1[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11955BenzoylhydrazineHCID 740491-Methyl-4-piperidoneHCID 4311764Sodium borohydride

Product 1

HCID 13799976N'-(1-Methylpiperidin-4-yl)benzohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

272 g (2 mol) of benzoic acid hydrazide are added to 1500 ml of methanol with stirring. Over 1 hour, 226 g (2 mol) of 1-methyl-4-piperidinone are then added dropwise at a temperature of 30° C. Slight cooling is necessary. The reaction mixture is stirred for half an hour at 30° C. and then for a further 1 hour at 60° C. The solution is then cooled to 0° C. and over a period of 2 hours 68 g (1.8 mol) NaBH4 is added using a spatula (strong foaming). Towards the end of the addition the mixture is warmed to room temperature. The solvent is evaporated off using a rotary evaporator and to the residue 900 g ice and 1000 ml dichloromethane are added with stirring. The organic phase is separated using a separating funnel and the aqueous phase is shaken twice with 300 ml dichloromethane in each case. The combined organic fractions are dried over MgSO4, the dichloromethane evaporated off and the residue recrystallized in 1 liter of isopropanol with the addition of 10 g active charcoal. The reaction product is dried in a drying cupboard at 50° C. in vacuo. (M.p. 149°-150° C.).

Workup

  1. temperatureSlight cooling
  2. stirringThe reaction mixture is stirred for half an hour at 30° C.
  3. waitfor a further 1 hour at 60° C
  4. additionis added
  5. additionTowards the end of the addition the mixture
  6. customThe solvent is evaporated off
  7. customa rotary evaporator
  8. additionto the residue 900 g ice and 1000 ml dichloromethane are added
  9. stirringwith stirring
  10. customThe organic phase is separated
  11. stirringthe aqueous phase is shaken twice with 300 ml dichloromethane in each case
  12. dry with materialThe combined organic fractions are dried over MgSO4
  13. customthe dichloromethane evaporated off
  14. customthe residue recrystallized in 1 liter of isopropanol with the addition of 10 g active charcoal
  15. customThe reaction product is dried in a drying cupboard at 50° C. in vacuo

Sources & evidence

ORD record
ord-9daf8b8ae3024ab1aac401ab32024b4e
Source dataset
uspto-grants-1989_06
Patent number
US04841047

Reaction notes

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