HCID 14304665, compound → HCID 14304651, compound

HRID 414058Notes

Reaction equation

HRID 414058 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH:17]([O:22][C:23]3[C:32]([N+:33]([O-])=O)=[CH:31][C:30]4[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=4[CH:24]=3)[C:18]([O:20]C)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>C(O)(=O)C.O.[Fe]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH:17]3[O:22][C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][C:32]=4[NH:33][C:18]3=[O:20])[CH2:29][CH2:28][CH2:27][CH2:26]5)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 14304665HCID 14304665, compound

Product 1

HCID 14304651HCID 14304651, compoundYield 43.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In a mixture of acetic acid (15 ml) and water (2.5 ml) was dissolved methyl 5-[4-(4-fluorophenyl)-1-piperazinyl]-2-(5,6,7,8-tetrahydro-3-nitro-2-naphthyloxy)valerate (4.1 g). To the solution was added little by little iron powder (1.9 g) whil stirring. The reaction was allowed to proceed for 30 minutes, followed by stirring at 80° C. for further 15 minutes. The resultant precipitate was filtered off, and the filtrate was concentrated. To the concentrate was added water, which was neutralized with an aqueous solution of sodium carbonate, followed by extraction with chloroform (then precipitated inorganic substances were filtered off). The chloroform layer was washed with water and dried (MgSO4). The concentrate was recrystallized from chloroform--ethyl acetate to give 1.54 g (43.1%) of 2-{3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}-6,7,8,9-tetrahydro-2H-naphtho[2,3-b][1,4]oxazin-3(4H)-one as crystals, m.p. 164°-165° C. This product was in good agreement with the authentic sample obtained by Method A.

Workup

  1. stirringby stirring at 80° C. for further 15 minutes
  2. filtrationThe resultant precipitate was filtered off
  3. concentrationthe filtrate was concentrated
  4. additionTo the concentrate was added water, which
  5. extractionfollowed by extraction with chloroform (
  6. customthen precipitated inorganic substances
  7. filtrationwere filtered off)
  8. washThe chloroform layer was washed with water
  9. dry with materialdried (MgSO4)
  10. customThe concentrate was recrystallized from chloroform

Sources & evidence

ORD record
ord-fde83796880144df986392a1c4e9928d
Source dataset
uspto-grants-1988_12
Patent number
US04789675

Reaction notes

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