Triethylamine → tert-Butyl 4-(6-chloropyridazin-3-yl)piperazine-1-carboxylate

HRID 2376650Notes

Reaction equation

HRID 2376650 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[N:16]=[N:17][C:18](Cl)=[CH:19][CH:20]=1.C(N(CC)CC)C>C(O)CCC>[Cl:14][C:15]1[N:16]=[N:17][C:18]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 673313,6-DichloropyridazineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 21925370tert-Butyl 4-(6-chloropyridazin-3-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 13.52 g of tert-butyl 1-piperazinecarboxylate, 10.81 g of 3,6-dichloropyridazine and 20 ml of triethylamine in 100 ml of n-butanol is heated at reflux for 5 hours. It is concentrated under vacuum and the residue is chromatographed on silica gel, eluting with a DCM/AcOEt (90/10; v/v) mixture. This gives 14 g of the expected product, which is used as it is.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 5 hours
  3. concentrationIt is concentrated under vacuum
  4. customthe residue is chromatographed on silica gel
  5. washeluting with a DCM/AcOEt (90/10; v/v) mixture

Sources & evidence

ORD record
ord-f5fa0cee2a264334bc8600cf6b524e5c
Source dataset
uspto-grants-2008_12
Patent number
US07468368B2

Reaction notes

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