Hydrazine → HCID 68432913, compound

HRID 1867371Notes

Reaction equation

HRID 1867371 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][NH2:21].CCN=C=NC[CH2:28][CH2:29]N(C)C.[OH:33]S([O-])(=O)=O.[K+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]([NH:20][NH:21][C:28](=[O:33])[CH3:29])=[O:19])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 9321HydrazineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516920Potassium bisulfateHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Product 1

HCID 68432913HCID 68432913, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 0.80 g (3.04 mmol) of 1-[(benzyloxy)carbonyl]-4-piperidinecarboxylic acid and 0.25 g (3.34 mmol) in 28 ml CH2Cl2 of N-acethyl hydrazine was treated at 0° C. with 0.73 g (3.80 mmol) of EDCI. Over night, the suspension was naturally warmed to RT, poured on aqueous 10% KHSO4 solution and extracted with CH2Cl2 (3×). The organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl, dried (Na2SO4) and evaporated to give 0.84 g (87%) of the title compound as white solid. MS: 320.2 (MH+).

Workup

  1. waitOver night
  2. extractionextracted with CH2Cl2 (3×)
  3. washThe organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-025397265d7147d6a42a9252bb424b60
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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