4-Methylmorpholine → 6-[(8-chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)carbonyl]-N-(4-pyridinylmethyl)-2-pyridinecarboxamide, hydrochloride

HRID 37356

Reaction equation

HRID 37356 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[O:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=[N:10][C:4]=2[CH:3]=1.[N:17]1[C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=[CH:19][C:18]=1[C:26](Cl)=[O:27].CN1CCOCC1.[NH2:36][CH2:37][C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1>C(Cl)(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[O:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][N:10]([C:23]([C:22]3[N:17]=[C:18]([C:26]([NH:36][CH2:37][C:38]4[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=4)=[O:27])[CH:19]=[CH:20][CH:21]=3)=[O:24])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 773174-PyridinemethanamineHCID 773352,6-Pyridinedicarbonyl dichlorideHCID 8382678-Chloro-dibenz[b,f]-[1,4]oxazepine

Product 1

HCID 1317190146-[(8-chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)carbonyl]-N-(4-pyridinylmethyl)-2-pyridinecarboxamide, hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 8-chloro-dibenz[b,f][1,4]oxazepine (0.77 g), 2,6-pyridine-dicarbonyl chloride (0.68 g) and 4-methylmorpholine (0.367 mL) in CHCl3 (33 mL) was allowed to stand at ambient temperature for 16 hours. To this solution was added 4-(aminomethyl)pyridine (0.34 mL) and the mixture was allowed to stand at ambient temperature for 16 hours. The mixture was concentrated and the residue was extracted with ethyl acetate and saturated NaHCO3. The organic extract was concentrated and the residue chromatographed over silica gel using 50% ethyl acetate in hexane. Appropriate fractions were pooled and concentrated to give the free base of the title compound as a white solid. The HCl salt of the free base was made as described in Example 3.

Workup

  1. waitto stand at ambient temperature for 16 hours
  2. concentrationThe mixture was concentrated
  3. extractionthe residue was extracted with ethyl acetate and saturated NaHCO3
  4. extractionThe organic extract
  5. concentrationwas concentrated
  6. customthe residue chromatographed over silica gel using 50% ethyl acetate in hexane
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f8ddeab8d46441a4b8fa8589c29649fd
Source dataset
uspto-grants-1995_05
Patent number
US05420270

Linked notes

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