4-Chloroquinazoline → HCID 10407202, compound

HRID 2118979Notes

Reaction equation

HRID 2118979 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][N:21]=1>CC(C)=O>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 788644-ChloroquinazolineHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 10407202HCID 10407202, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (2.48 g) and 4-chloroquinazoline (1.64 g) were stirred in acetone (30 ml) at room temperature for 7 days. The acetone was evaporated and the oily residue was dissolved in 2 Normal hydrochloric acid. The acidic solution was extracted with ethyl acetate. The aqueous solution was then basified to pH 9 and was extracted with ethyl acetate. A solid crystallised from the basic ethyl acetate extract and was collected and dissolved in chloroform. The chloroform solution was washed with water, dried and evaporated to dryness. The residue was recrystallised from ethyl acetate to yield the title compound (0.6 g), m.p. 111° C.

Workup

  1. customThe acetone was evaporated
  2. dissolutionthe oily residue was dissolved in 2 Normal hydrochloric acid
  3. extractionThe acidic solution was extracted with ethyl acetate
  4. extractionwas extracted with ethyl acetate
  5. customA solid crystallised from the basic ethyl acetate
  6. extractionextract
  7. customwas collected
  8. dissolutiondissolved in chloroform
  9. washThe chloroform solution was washed with water
  10. customdried
  11. customevaporated to dryness
  12. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-2ad690010f1746ce9acb85b7a75a526d
Source dataset
uspto-grants-1987_07
Patent number
US04681883

Reaction notes

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