Hydrochloric Acid → Nonan-3-ylhydrazine

HRID 566322Notes

Reaction equation

HRID 566322 reaction equation
[CH2:1]([C:3](=[N:10][NH:11]C(OC(C)(C)C)=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH3:2].C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>C1COCC1.CO>[CH2:1]([CH:3]([NH:10][NH2:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 72599204tert-Butyl N'-(1-ethyl-heptylidene)-hydrazinecarboxylate

Product 1

HCID 21266080Nonan-3-ylhydrazine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

34.84 g (135.9 mmol) of tert-butyl N′-(1-ethyl-heptylidene)-hydrazinecarboxylate are dissolved in a mixture of 100 ml of THF and 150 ml of methanol and, after 9.93 g (157.6 mmol) of sodium cyanoborohydride have been added, the mixture is stirred for 2 hours at room temperature. 97 ml of 6N HCl are added dropwise and, after the addition has ended, the mixture is refluxed for 1.5 hours. It is neutralized with 6N NaOH solution, then, after the non-aqueous solvents have been removed, extracted three times with dichloromethane, and, after the mixture has been dried over sodium sulphate, the solvent is removed in vacuo. This gives 19.78 g (92%) of a yellow oil.

Workup

  1. additionafter the addition
  2. temperaturethe mixture is refluxed for 1.5 hours
  3. customafter the non-aqueous solvents have been removed
  4. extractionextracted three times with dichloromethane
  5. dry with materialafter the mixture has been dried over sodium sulphate
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-77dc437b6af2457281698d50b05ad448
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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