Diisopropyl Ether → HCID 19087684, compound

HRID 1464286Notes

Reaction equation

HRID 1464286 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23](=[O:30])[NH:22][C:21]2=[O:31])[CH2:12][CH2:11]1)([O-])=O.[Sn](Cl)Cl.C(OC(C)C)(C)C>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23](=[O:30])[NH:22][C:21]2=[O:31])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 24479Stannous ChlorideHCID 19087663HCID 19087663, compound

Product 1

HCID 19087684HCID 19087684, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-[4-{4-(2-nitrophenyl)piperazin-1-yl}butyl]-2,4(1H,3H)-quinazolinedione (90 mg) in ethanol (8 ml) was added tin(II) chloride (159 mg) at 80° C. After stirring for 1 hour at the same temperature, the reaction mixture was quenched with ice and saturated aqueous sodium bicarbonate, and extracted with chloroform. The organic extract was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and evaporated to give an amorphous. 1-[4-{4-(2-Aminophenyl)piperazin-1-yl)butyl]-2,4(1H,3H)-quinazolinedione (31 mg) was obtained by crystallization of the amorphous from diisopropyl ether.

Workup

  1. customthe reaction mixture was quenched with ice and saturated aqueous sodium bicarbonate
  2. extractionextracted with chloroform
  3. extractionThe organic extract
  4. washwas washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give an amorphous

Sources & evidence

ORD record
ord-28be445cd86d4458a8b7497459957913
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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