Phosgene → 3-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-6-methoxy-2,4(1H,3H)-quinazolinedione

HRID 496892Notes

Reaction equation

HRID 496892 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:11][CH2:10]1)=[O:5].[C:30](Cl)(Cl)=[O:31].C(OCC)(=O)C.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[Cl:22])[O:15][CH:12]1[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:27][CH:26]=[C:25]([O:28][CH3:29])[CH:24]=3)[NH:1][C:30]2=[O:31])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 223222332-Amino-N-{2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethyl}-5-methoxybenzamide

Product 1

HCID 223223843-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-6-methoxy-2,4(1H,3H)-quinazolinedione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The product of step (i) above was dissolved in toluene (10 ml). A solution of phosgene 2.0 M in toluene (10 ml) was added, the solution heated under reflux for 1 hour and cooled. Ethyl acetate and aqueous NaHCO3 solution were added, the organic phase separated, dried and concentrated to leave a residue which was purified by chromatography (dichloromethane:methanol, 95:5). The titled product was obtained as a solid (0.11 g).

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. customthe organic phase separated
  5. customdried
  6. concentrationconcentrated
  7. customto leave a residue which
  8. customwas purified by chromatography (dichloromethane:methanol, 95:5)

Sources & evidence

ORD record
ord-0aee52b8baa14e5798f4d5458a8dace4
Source dataset
uspto-grants-2005_09
Patent number
US06946478B2

Reaction notes

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