Acetone → HCID 70874615, compound

HRID 2172277Notes

Reaction equation

HRID 2172277 reaction equation
C[O:2][C:3]1(OC)[CH2:8][CH2:7][N:6]([C:9]2[CH:28]=[CH:27][C:12]([O:13][CH2:14][C@@H:15]3[O:20][C:19]4=[N:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][N:18]4[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.CC(C)=O.Cl>O>[N+:24]([C:22]1[N:21]=[C:19]2[N:18]([CH:23]=1)[CH2:17][CH2:16][C@H:15]([CH2:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([N:6]3[CH2:5][CH2:4][C:3](=[O:2])[CH2:8][CH2:7]3)=[CH:28][CH:27]=1)[O:20]2)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 86709411HCID 86709411, compound

Product 1

HCID 70874615HCID 70874615, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-7-[4-(4,4-Dimethoxypiperidin-1-yl)phenoxymethyl]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (5.16 g), acetone (100 ml) and water (17 ml) were mixed. A 6 N hydrochloric acid aqueous solution (41 ml) was added thereto, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The remaining water layer was ice-cooled and neutralized by adding a 20% sodium carbonate aqueous solution. After being stirred at the same temperature for 10 minutes, the precipitated crystal was collected by filtration. The crystal thus obtained was dried at 60° C. to afford the title compound as a yellow solid (4.57 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. temperaturecooled
  3. additionby adding a 20% sodium carbonate aqueous solution
  4. stirringAfter being stirred at the same temperature for 10 minutes
  5. filtrationthe precipitated crystal was collected by filtration
  6. customThe crystal thus obtained
  7. customwas dried at 60° C.

Sources & evidence

ORD record
ord-d7cdb82536bf4bff9b339cd68cedcc42
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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