4-Methylmorpholine → HCID 86755933, compound

HRID 366781Notes

Reaction equation

HRID 366781 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][O:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[C:8](=[C:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:5]2=[N:6][CH:7]=1.[N+:24]1([O-])[CH:29]=[CH:28][C:27]([CH2:30][C:31](O)=[O:32])=[CH:26][CH:25]=1.C1C=CC2N([OH:44])N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CN1CCOCC1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][O:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[C:8](=[C:18]3[CH2:23][CH2:22][N+:21]([O-:44])([C:31](=[O:32])[CH2:30][C:27]4[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=4)[CH2:20][CH2:19]3)[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3815830HCID 3815830, compoundHCID 15895407HCID 15895407, compound

Product 1

HCID 86755933HCID 86755933, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-(3-Bromo-8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ylidene)-piperidine (270 mg, 0.68 mmol), 4-pyridine-acetic acid 1-oxide (260 mg, 1.69 mmol), HOBT (200 mg, 1.48 mmol), and EDCl (320 mg, 1.67 mmol) were mixed and stirred at 0° C. in DMF (10 ml, anhydrous). NMM (0.5 ml, 4.53 mmol) was added, and the reaction mixture was stirred 2 hours at 0° C. and then overnight at 20° C. The solvent was evaporated off, water (20 ml) was added, and the mixture was extracted with methylene chloride (3×50 ml) and the extract was dried (MgSO4), filtered and evaporated, yielding a crude product which was chromatographed on silica gel and eluted with 12%ethylacetate/hexanes containing 2% ammonium hydroxide. The product was recrystallized from ether to afford a white powder, 4-(3-bromo-8-chloro-5,11-dihydro[1]benz-oxepino[4,3-b]pyridin-11-ylidene)-1-(4-pyridine-acetyl)piperidine N1-oxide (260 mg, 72%); MS (FAB, M+H)=526.

Workup

  1. customovernight
  2. customat 20° C
  3. customThe solvent was evaporated off
  4. additionwater (20 ml) was added
  5. extractionthe mixture was extracted with methylene chloride (3×50 ml)
  6. dry with materialthe extract was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customyielding a crude product which
  10. customwas chromatographed on silica gel
  11. washeluted with 12%ethylacetate/hexanes containing 2% ammonium hydroxide
  12. customThe product was recrystallized from ether

Sources & evidence

ORD record
ord-3f1f59b0cf10490983af2688a8a17418
Source dataset
uspto-grants-2000_10
Patent number
US06130229

Reaction notes

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