HCID 22449736, compound → HCID 22449621, compound

HRID 2187064Notes

Reaction equation

HRID 2187064 reaction equation
[O:1]=[C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]([N+:13]([O-])=O)=[CH:7][CH:8]=2)[N:3]1[CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([O:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:22][CH2:21]1>Cl.O.C(O)C.O1CCCC1.[Zn]>[NH2:13][C:6]1[CH:5]=[C:4]2[C:9]([C:10](=[O:12])[NH:11][C:2](=[O:1])[N:3]2[CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([O:26][CH:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:22][CH2:21]2)=[CH:8][CH:7]=1

Participants

7

Reactant 1

HCID 22449736HCID 22449736, compound

Product 1

HCID 22449621HCID 22449621, compoundYield 69%

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dioxo-1-[4-(4-diphenylmethoxypiperidino)butyl]-7-nitro-1,2,3,4-tetrahydroquinazoline (3.00 g) obtained in Example 11 was dissolved in a mixture of concentrated hydrochloric acid (10.0 ml), water (50.0 ml), ethanol (50.0 ml) and tetrahydrofuran (50.0 ml) and an excess of zinc powder was added in portions. After completion of the reaction, the reaction mixture was filtered, and the filtrate was made basic with 25% aqueous ammonia solution and extracted with ethyl acetate. After the extract was washed with water and dried (Na2SO4), the solvent was distilled off under reduced pressure to give the title compound (1.95 g, 69%). Recrystallization from ethyl acetate yielded a yellow crystal having a melting point of 162 to 164° C.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. extractionextracted with ethyl acetate
  4. washAfter the extract was washed with water
  5. dry with materialdried (Na2SO4)
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6e05179d912840f69a40df3cad2614b3
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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