Bromine → HCID 23065416, compound

HRID 1782702Notes

Reaction equation

HRID 1782702 reaction equation
C([O-])(=O)C.[Na+].[NH:6]1[CH2:11][CH2:10][CH:9]([N:12]2[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:22])[CH2:8][CH2:7]1.[Br:23]Br>C(O)(=O)C.O>[BrH:23].[Br:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:22])[N:12]([CH:9]1[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]1)[CH2:21]2

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one

Product 1

HCID 23065416HCID 23065416, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
14 °C

Procedure

To a solution of 6.16 g (0.075 mol) of sodium acetate and 11.565 g (0.05 mol) of 3,4-dihydro-3-(4-piperidinyl)-2(1H)-quinazolinone in a mixture of 150 ml of glacial acetic acid and 35 ml of water a solution of 8.8 g (0.055 mol) of anhydrous bromine in 20 ml of glacial acetic acid was added dropwise, with stirring and whilst maintaining a reaction temperature of 13 to 15° C. The mixture was filtered and the filtrate was evaporated down in vacuo. To remove any inorganic components the residue was taken up five times in 50 ml of dichloromethane, filtered and evaporated down, then triturated with a little acetonitrile, whereupon crystallisation occurred. The crystals were suction filtered, washed with acetonitrile/diethylether (1/1 v/v) and after drying in vacuo 5.5 g of colourless crystals of melting point 288° C. (decomposition) were obtained. By working up the mother liquors a further 4.5 g of material of the same quality was obtained. Total yield: 10.0 g (51% of theory).

Workup

  1. additionwas added dropwise
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated down in vacuo
  4. customTo remove any inorganic components the residue
  5. filtrationfiltered
  6. customevaporated down
  7. customtriturated with a little acetonitrile, whereupon crystallisation
  8. filtrationfiltered
  9. washwashed with acetonitrile/diethylether (1/1 v/v)
  10. dry with materialafter drying in vacuo 5.5 g of colourless crystals of melting point 288° C. (decomposition)
  11. customwere obtained
  12. customwas obtained

Sources & evidence

ORD record
ord-de5f82b46ecb4eeab685bf270778f146
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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