1,3-Benzodioxol-5-amine → HCID 14650689, compound

HRID 982265Notes

Reaction equation

HRID 982265 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.[N+](C1C=CC([O:18][C:19]([O:21][CH:22]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:26][C:25]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[N:24][CH2:23]2)=O)=CC=1)([O-])=O>CN(C)C1C=CN=CC=1.C(#N)C>[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH:6][C:19]([O:21][CH:22]3[CH:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[O:26][C:25]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[N:24][CH2:23]3)=[O:18])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 2

HCID 843101,3-Benzodioxol-5-amineHCID 14650635HCID 14650635, compound

Product 1

HCID 14650689HCID 14650689, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

3,4-Methylenedioxyaniline (1.1 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of (5RS, 6SR)-5-(4-nitrophenoxycarbonyloxy)-2,6-diphenyl-5,6-dihydro-4H-1,3-oxazine (1.67 g) and 4-(dimethylamino)pyridine (0.2 g) in anhydrous acetonitrile (50 cc). The solution obtained is heated to reflux for 5 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is purified by chromatography on silica (0.063-0.2 mm; 50 g) contained in a column 2 cm in diameter [eluent: cyclohexane/ethyl acetate/triethylamine (65:30:5 by volume)], collecting 15-cc fractions. Fractions 3 to 6 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in diisopropyl ether, (5RS, 6SR)-5-(3,4-methylenedioxyphenylcarbamoyloxy)-2,6-diphenyl-5,6-dihydro-4H-1,3-oxazine (0.8 g), m.p. 138° C., is obtained.

Workup

  1. customThe solution obtained
  2. temperatureis heated
  3. temperatureto reflux for 5 hours
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe oil obtained
  6. customis purified by chromatography on silica (0.063-0.2 mm; 50 g)
  7. customcollecting 15-cc fractions
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  9. customAfter recrystallization in diisopropyl ether

Sources & evidence

ORD record
ord-b23f349de079480ba2c3d39f511e51c2
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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