HCID 14304627, compound → HCID 14304632, compound

HRID 414059Notes

Reaction equation

HRID 414059 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]3[C:22](=[O:23])[NH:21][C:20]4[CH:24]=[C:25]([N+:28]([O-])=O)[CH:26]=[CH:27][C:19]=4[O:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>CO.O1CCCC1.[Pd]>[NH2:28][C:25]1[CH:26]=[CH:27][C:19]2[O:18][CH:17]([CH2:16][CH2:15][CH2:14][N:11]3[CH2:12][CH2:13][N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:9][CH2:10]3)[C:22](=[O:23])[NH:21][C:20]=2[CH:24]=1

Participants

5

Reactant 1

HCID 14304627HCID 14304627, compound

Product 1

HCID 14304632HCID 14304632, compoundYield 98.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of methanol (80 ml) and tetrahydrofuran (20 ml) was dissolved 2-{3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}-6-nitro-2H-1,4-benzoxazin-3(4H)-one (2.03 g). To the solution was added 10% Pd - C (50% wet, 0.6 g) to conduct catalytic reduction. After the absorption of hydrogen finished, the catalyst was filtered off, and the filtrate was concentrated. The residue was crystallized from ethanol to give 1,85 g (98.2%) of 6-amino-2-{3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}-2H-1,4-benzoxazin-3(4H)-one, m.p. 158°-159° C.

Workup

  1. customAfter the absorption of hydrogen
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-0043011f12b24705a5304f13b27bbbe4
Source dataset
uspto-grants-1988_12
Patent number
US04789675

Reaction notes

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