4-Methylmorpholine → HCID 86755934, compound

HRID 366784Notes

Reaction equation

HRID 366784 reaction equation
[Br:1][C:2]1[C:3]([Cl:23])=[CH:4][C:5]2[O:15][CH2:14][C:13]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:6]=2[CH:22]=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[C:3]([Cl:23])=[CH:4][C:5]2[O:15][CH2:14][C:13]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[C:16]3[CH2:17][CH2:18][N+:19]([O-:44])([C:31](=[O:32])[CH2:30][C:27]4[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=4)[CH2:20][CH2:21]3)[C:6]=2[CH:22]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3815830HCID 3815830, compoundHCID 23289881HCID 23289881, compound

Product 1

HCID 86755934HCID 86755934, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

4-(9-Bromo-8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ylidene)-piperidine (130 mg, 0.33 mmol), 4-pyridine-acetic acid 1-oxide (130 mg, 0.85 mmol), HOBT (120 mg, 0.89 mmol), and EDCl (160 mg, 0.83 mmol) were stirred at 0° C. in DMF (5 ml, anhydrous). N-Methyl-morpholine (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 (2×100 ml) and water (30 ml). The organic layer was separated and dried (MgSO4), filtered and evaporated, yielding an oil which was chromatographed on silica gel and eluted with 15%methanol/ethylacetate containing 2% ammonium hydroxide. The product was obtained as a white solid, 4-(9-bromo-8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ylidene)-1-(4-pyridine-acetyl)piperidine N1-oxide (170 mg, 98%). MS (FAB, M+H)=526.

Workup

  1. customThe solvent was evaporated off
  2. extractionthe residue was extracted with methylene chloride (2×100 ml) and water (30 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 15%methanol/ethylacetate containing 2% ammonium hydroxide

Sources & evidence

ORD record
ord-cce99bd4551c48fc8ec4a24460c51f44
Source dataset
uspto-grants-2000_10
Patent number
US06130229

Reaction notes

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