Borane → (1-Tert-butyl-piperidin-4-yl)-hydrazine

HRID 1350767Notes

Reaction equation

HRID 1350767 reaction equation
B.C1COCC1.C(OC([NH:14][N:15]=[C:16]1[CH2:21][CH2:20][N:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17]1)=O)(C)(C)C>Cl>[C:22]([N:19]1[CH2:18][CH2:17][CH:16]([NH:15][NH2:14])[CH2:21][CH2:20]1)([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 6331BoraneHCID 8028TetrahydrofuranHCID 48916874Tert-butyl 2-(1-tert-butylpiperidin-4-ylidene)hydrazinecarboxylate

Product 1

HCID 21097250(1-Tert-butyl-piperidin-4-yl)-hydrazine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

A 1M solution borane in THF (28.7 mL, 28.7 mmol) was added to N′-(1-tert-Butyl-piperidin-4-ylidene)-hydrazinecarboxylic acid tert-butyl ester. The mixture was stirred for 16 h, and then 40 mL of 6M HCl was added. The mixture was heated to 60° C. for 30 min. The mixture was concentrated and 200 mL of petroleum ether was added, followed by powdered NaOH (5 g). The slurry was stirred manually for 30 min, and then the mixture was dried with MgSO4, filtered, and concentrated to give 1.21 g of (1-tert-butyl-piperidin-4-yl)-hydrazine (1.21 g).

Workup

  1. concentrationThe mixture was concentrated
  2. addition200 mL of petroleum ether was added
  3. stirringThe slurry was stirred manually for 30 min
  4. dry with materialthe mixture was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7832bc38d01345dfad88520760c55e37
Source dataset
uspto-grants-2007_05
Patent number
US07214802B2

Reaction notes

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