N-1,4-Benzodioxane-2-carbonyl piperazine → HCID 86736817, compound

HRID 1448961Notes

Reaction equation

HRID 1448961 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[C:4]([Cl:18])[N:3]=1.[O:19]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][CH2:21][CH:20]1[C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30]>C(O)CCC>[ClH:18].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[C:4]([N:34]2[CH2:35][CH2:36][N:31]([C:29]([CH:20]3[O:19][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[O:22][CH2:21]3)=[O:30])[CH2:32][CH2:33]2)[N:3]=1

Participants

4

Reactant 2

HCID 2735449N-1,4-Benzodioxane-2-carbonyl piperazineHCID 20351338HCID 20351338, compound

Product 1

HCID 86736817HCID 86736817, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Amino-2-chloro-6,7-diethoxyquinazoline (0.33 g.) and N-(1,4-benzodioxan-2-carbonyl)piperazine (0.32 g.) were heated under reflux in n-butanol (30 ml.) overnight. The mixture was then evaporated in vacuo and the residue partitioned between sodium carbonate solution and chloroform. The combined chloroform extracts were washed with water, dried (Na2SO4), evaporated in vacuo and the residue chromatographed on silica gel (70 g.) using chloroform/methanol (0-5%) as eluent. Similar fractions were combined, evaporated in vacuo then redissolved in chloroform/methanol and treated with ethereal hydrogen chloride. The solution was then evaporated in vacuo and the residue recrystallized from isopropanol to give 4-amino-2-[4-(1,4-benzodioxan-2-carbonyl)piperazin-1-yl]-6,7-diethoxyquinazoline hydrochloride.2 1/2 hydrate (0.19 g.), m.p. 180°-184° C. (decomp.)

Workup

  1. customThe mixture was then evaporated in vacuo
  2. customthe residue partitioned between sodium carbonate solution and chloroform
  3. washThe combined chloroform extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customthe residue chromatographed on silica gel (70 g.)
  7. customevaporated in vacuo
  8. dissolutionthen redissolved in chloroform/methanol
  9. additiontreated with ethereal hydrogen chloride
  10. customThe solution was then evaporated in vacuo
  11. customthe residue recrystallized from isopropanol

Sources & evidence

ORD record
ord-ae62e86b47fe457c9605636a2eeffc99
Source dataset
uspto-grants-1980_02
Patent number
US04188390

Reaction notes

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