Hydrochloric Acid → HCID 19921654, compound

HRID 1647806Notes

Reaction equation

HRID 1647806 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1)([O-])=O.O.Cl>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19921653HCID 19921653, compound

Product 1

HCID 19921654HCID 19921654, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mechanically stirred solution of ethyl 4-(3-nitro-4-pyridinyl)-1-piperazinecarboxylate (10 g, 35.7 mmol) and iron filings [40 mesh](21.7 g, 389 mmol) in a mixture of 50 mL of ethanol, 7 mL of water and 0.36 mL of concentrated HCl was heated to reflux for 4 h. The hot solution was filtered and concentrated in vacuo to give of ethyl 4-(3-amino-4-pyridinyl)-1-piperazinecarboxylate (8.5 g, 95%). An analytical sample was obtained by recrystallization from ethyl acetate in hexanes: mp 141°-142° C. Anal. Calcd for C12H18N4O2 : C, 57.58; H, 7.25; N, 22.38. Found: C, 57.43; H, 7.19; N, 22.24.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. filtrationThe hot solution was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c009fbc74044454a8a6e2593a636bd0
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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