Diethyl Ether → tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

HRID 604988Notes

Reaction equation

HRID 604988 reaction equation
C(C1NC=CN=1)(C1NC=CN=1)=O.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26]([OH:28])=O)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[NH2:29][NH2:30].C(OCC)C>C(Cl)Cl>[NH:29]([C:26]([CH:23]1[CH2:24][CH2:25][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:21][CH2:22]1)=[O:28])[NH2:30]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9321HydrazineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Carbonyl diimidazole (3.57 g, 22 mmol) was added to a solution of 1-(tert-butoxycarbonyl)-piperidine-4-carboxylic acid (4.59 g, 20 mmol) in methylene chloride (50 mL) and stirred for two hours until gas evolution ceased. Then hydrazine (0.8 mL, ˜26 mmol) was added to the reaction and the reaction was stirred at room temperature for another two hours. The reaction was diluted with more methylene chloride and washed with sat'd aqueous NaHCO3. The organic layer was dried over anhydrous Na2SO4, filtered and the solvent evaporated to give a viscous residue. Trituration with diethyl ether afforded tert-butyl 4-(hydrazinocarbonyl)-piperidine-1-carboxylate as an off-white solid. 1H NMR (500 MHz, CDCl3): 6.77 (1H, br s), 4.15 (2H, br s), 3.90 (2H, v br s), 2.75 (2H, b s), 2.22 (1H, m), 1.78 (2H, br d, J=11.9 Hz), 1.66 (2H, br q, J=12.2 Hz, J=27.5 Hz), 1.47 (9H, s).

Workup

  1. stirringthe reaction was stirred at room temperature for another two hours
  2. washwashed with sat'd aqueous NaHCO3
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customto give a viscous residue

Sources & evidence

ORD record
ord-75f82b9ff9184b099fe09421c5f92562
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

Loading…