Diethyl Ether → HCID 21073427, compound

HRID 1373623Notes

Reaction equation

HRID 1373623 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH:16]=O)=[N:11][C:4]=2[NH:3]1.[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CCOCC>ClC(Cl)C>[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[N:26]1[CH2:31][CH2:30][N:29]([CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:10]2[CH:9]=[CH:8][C:5]3[O:6][CH2:7][C:2](=[O:1])[NH:3][C:4]=3[N:11]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8518331-(2,3-Dichlorophenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 21073341HCID 21073341, compound

Product 1

HCID 21073427HCID 21073427, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of 4-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yloxy)-butyraldehyde (0.325 g, 1.37 mmol) in dichloroethane (6 mL) was added a solution of 1-(2,3-dichloro-phenyl)-piperazine (0.318 g, 1.37 mmol) in dichloroethane (3 mL) via cannula. The mixture was stirred for 20 minutes at room temperature and NaBH(OAc)3 (0.377 g, 1.78 mmol) was added. The reaction was stirred for 2.5 h and quenched with saturated NaHCO3 and water. The mixture was extracted with EtOAc and the organic layer was washed with saturated NaHCO3, water and brine, dried over Na2SO4 and concentrated. Purification by chromatography on silica gel (0–5% MeOH/CH2Cl2) gave a foam. Et2O was added and product crashed out. The precipitate was filtered and dried to give the title compound as a white solid (0.386 g, 0.854 mmol, 63%). MS: APCI: M+1: 451.1 (Exact Mass: 450.12).

Workup

  1. stirringThe reaction was stirred for 2.5 h
  2. customquenched with saturated NaHCO3 and water
  3. extractionThe mixture was extracted with EtOAc
  4. washthe organic layer was washed with saturated NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by chromatography on silica gel (0–5% MeOH/CH2Cl2)
  8. customgave a foam
  9. filtrationThe precipitate was filtered
  10. customdried

Sources & evidence

ORD record
ord-758e6134150a4bdeaf2a82c0c3f8012f
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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