Diphenyl Ether → Ethyl 4-[2-(8-chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)-3,4-dioxo-1-cyclobuten-1-yl]-1-phenyl-2-piperazinecarboxylate

HRID 1707576

Reaction equation

HRID 1707576 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.C([O:19][C:20]1[C:23](=[O:24])[C:22](=O)[C:21]=1[N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:28]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:27]1)C.C1(OC2C=CC=CC=2)C=CC=CC=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:22]3[C:23](=[O:24])[C:20](=[O:19])[C:21]=3[N:26]3[CH2:31][CH2:30][N:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:28]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:27]3)[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 7583Diphenyl EtherHCID 8382678-Chloro-dibenz[b,f]-[1,4]oxazepineHCID 18961721Ethyl 4-(2-ethoxy-3,4-dioxo-1-cyclobuten-1-yl)-1-phenyl-2-piperazinecarboxylate

Product 1

HCID 15232292Ethyl 4-[2-(8-chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)-3,4-dioxo-1-cyclobuten-1-yl]-1-phenyl-2-piperazinecarboxylateYield 43.8%

Procedure

A mixture of 8-chloro-dibenz[b,f][1,4]oxazepine (1.02 g) and the product of Example 3 (0.26 g) and diphenyl ether (3 mL) was heated to reflux for 1.75 hours. The mixture was rapidly filtered thourough a small column of silica gel and the filtrate was concentrated. The residue was purified by chromatography on silica gel to obtain the title compound (0.173 g).

Workup

  1. temperatureto reflux for 1.75 hours
  2. filtrationThe mixture was rapidly filtered thourough a small column of silica gel
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8896ec655f0f4652a1982053d00f9a88
Source dataset
uspto-grants-1994_10
Patent number
US05354746

Linked notes

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