Phosphorus tribromide → 4-[4-(2-Bromoethyl)piperidin-1-yl]-6,7-dimethoxyquinazoline

HRID 1154324Notes

Reaction equation

HRID 1154324 reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[N:13]=[CH:12][N:11]=[C:10]2[N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26]O)[CH2:21][CH2:20]1>C(O)C.C(N(CC)CC)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[N:13]=[CH:12][N:11]=[C:10]2[N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][Br:2])[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 20434942HCID 20434942, compound

Product 1

HCID 204348824-[4-(2-Bromoethyl)piperidin-1-yl]-6,7-dimethoxyquinazoline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

Phosphorus tribromide (9.7 g) was added at room temperature to a stirred solution of 1-(6,7-dimethoxyquinazolin-4-yl)-4-(2-hydroxyethyl)piperidine (7.5 g) in ethanol free chloroform (200 cm3) and triethylamine (5.0 cm3). After stirring for 16 hours the volatile material was removed in vacuo and the residue was taken into aqueous sodium carbonate solution and extracted with chloroform (3×50 cm3). The dried (MgSO4) extracts were evaporated and the residue was chromatographed on "Florisil" (Trade Mark, Hopkin and Williams) eluting with chloroform to afford 1-(6,7-dimethoxyquinazoline-4-yl)-4-(2-bromoethyl) piperidine 1/4 H2O as a white solid, m.p. 191° (5.6 g).

Workup

  1. customwas removed in vacuo
  2. extractionextracted with chloroform (3×50 cm3)
  3. dry with materialThe dried (MgSO4) extracts
  4. customwere evaporated
  5. customthe residue was chromatographed on "Florisil" (Trade Mark, Hopkin and Williams)
  6. washeluting with chloroform

Sources & evidence

ORD record
ord-b2adae7278e34603bda127715b09aa42
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Reaction notes

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