4-Methylmorpholine → HCID 86755932, compound

HRID 366780Notes

Reaction equation

HRID 366780 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[CH:6]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:7]3[C:12]([CH2:13][O:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3.[N+:23]1([O-])[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1.C1C=CC2N([OH:43])N=NC=2C=1.CCN=C=NCCCN(C)C.CN1CCOCC1>CN(C=O)C>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[CH:6]([N:15]3[CH2:16][CH2:17][N+:18]([O-:43])([C:30](=[O:31])[CH2:29][C:26]4[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=4)[CH2:19][CH2:20]3)[C:7]3[C:12]([CH2:13][O:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3815830HCID 3815830, compoundHCID 15780500HCID 15780500, compound

Product 1

HCID 86755932HCID 86755932, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

1-(8-Chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-yl)-piperazine (420 mg, 1.33 mmol), 4-pyridineacetic acid 1-oxide (280 mg, 2.07 mmol), HOBT (290 mg, 2.14 mmol), and EDCI (470 mg, 2.45 mmol) were stirred at 0C in DMF (5 ml, anhydrous). NMM (0.5 ml, 4.53 mmol) was added, and the reaction mixture was stirred overnight at 20° C. The solvent was evaporated off, and the residue was extracted with methylene chloride (200 ml) and water (100 ml). The organic layer was separated and dried (MgSO4), filtered and evaporated, yielding an oil which was chromatographed on silica gel and eluted with 20%methanol/ethylacetate containing 2% ammonium hydroxide. The product was obtained as a light yellow solid, 4-(8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-yl)-1-(4-pyridine-acetyl)-piperazine N1-oxide. MS (FAB, M+H)=451.

Workup

  1. customThe solvent was evaporated off
  2. extractionthe residue was extracted with methylene chloride (200 ml) and water (100 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customyielding an oil which
  8. customwas chromatographed on silica gel
  9. washeluted with 20%methanol/ethylacetate containing 2% ammonium hydroxide

Sources & evidence

ORD record
ord-22bcead8904c45ff86eb5a244415eb8e
Source dataset
uspto-grants-2000_10
Patent number
US06130229

Reaction notes

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