Hydrochloric Acid → 4-Hydrazinyl-1-methylpiperidine

HRID 2109261Notes

Reaction equation

HRID 2109261 reaction equation
B.[CH3:2][N:3]1[CH2:8][CH2:7][C:6](=[N:9][NH:10]C(OC(C)(C)C)=O)[CH2:5][CH2:4]1.Cl>C1COCC1>[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([NH:9][NH2:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 21097379Tert-butyl 2-(1-methylpiperidin-4-ylidene)hydrazinecarboxylate

Product 1

HCID 109205354-Hydrazinyl-1-methylpiperidineYield 81.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1 M borane in THF (30 mL) was added to solid 2.80 g (12.3 mmol) of tert-butyl N′-(1-Methyl-piperidin-4-ylidene)-hydrazinecarboxylate. The mixture was stirred under N2 for 16 h when 40 mL of 6M HCl was carefully added. The mixture was heated to 60° C. for 30 min. The mixture was concentrated in vacuo at ambient temperature for 2 days. Petroleum ether (200 mL) and powdered NaOH (5 g) were added, and the mixture was stirred manually for 30 min. The mixture was dried with MgSO4, filtered, and carefully concentrated to give 1.3 g of (1-methyl-piperidin-4-yl)-hydrazine.

Workup

  1. additionwas carefully added
  2. concentrationThe mixture was concentrated in vacuo at ambient temperature for 2 days
  3. additionPetroleum ether (200 mL) and powdered NaOH (5 g) were added
  4. dry with materialThe mixture was dried with MgSO4
  5. filtrationfiltered
  6. concentrationcarefully concentrated

Sources & evidence

ORD record
ord-7b6ff192016d496fbf220b53c76b1f33
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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