Cyclohexylamine → 3-Cyclohexyl-7-methoxy-3,4-dihydro-benzo[e][1,3]oxazin-2-one

HRID 2224039Notes

Reaction equation

HRID 2224039 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:10]=1[CH:11]=O.[BH4-].[Na+].[C:21](C1NC=CN=1)(C1NC=CN=1)=[O:22]>CCO.O>[CH:1]1([N:7]2[CH2:11][C:10]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:9]=3[O:8][C:21]2=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 7965CyclohexylamineHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 675254903-Cyclohexyl-7-methoxy-3,4-dihydro-benzo[e][1,3]oxazin-2-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

40 g of cyclohexylamine are added to a solution of 26 g of 2-hydroxy-4-methoxy-benzaldehyde in 800 ml of absolute EtOH at RT. The mixture obtained is stirred for 1.5 hours, cooled to 0°, and 20 g of NaBH4 are added in portions. The mixture obtained is stirred for 3 hours at RT, poured into H2O and the mixture obtained is extracted with CH2Cl2. Two phases are formed and are separated. The organic layer obtained is dried, 42 g of carbonyl-diimidazole are added and the mixture obtained is stirred for 16 hours at RT. Additional 21.5 g of carbonyl-diimidazole are added, the mixture obtained is stirred for 3 hours, washed with 1N HCl, a saturated, aqueous solution of NaHCO3 and brine, dried and concentrated in vacuo. 3-Cyclohexyl-7-methoxy-3,4-dihydrobenzo[e][1,3]-oxazin-2-one is obtained. m.p.: 76-77°.

Workup

  1. customThe mixture obtained
  2. temperaturecooled to 0°
  3. customThe mixture obtained
  4. stirringis stirred for 3 hours at RT
  5. customthe mixture obtained
  6. extractionis extracted with CH2Cl2
  7. customTwo phases are formed
  8. customare separated
  9. customThe organic layer obtained
  10. customis dried
  11. addition42 g of carbonyl-diimidazole are added
  12. customthe mixture obtained
  13. stirringis stirred for 16 hours at RT
  14. customthe mixture obtained
  15. stirringis stirred for 3 hours
  16. washwashed with 1N HCl
  17. dry with materiala saturated, aqueous solution of NaHCO3 and brine, dried
  18. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3325a90b365742d09ddba111fb6fce84
Source dataset
uspto-grants-2008_05
Patent number
US07378416B2

Reaction notes

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