Potassium Carbonate → 4-(2-Keto-1-benzimidazolinyl)-1-[2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]piperidine

HRID 580045Notes

Reaction equation

HRID 580045 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.CS(O[CH2:22][CH2:23][C:24]1[CH:39]=[CH:38][C:27]2[O:28][CH2:29][C:30]3[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=3[C:32](=[O:33])[C:26]=2[CH:25]=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>C(O)C.CO.C(OCC)(=O)C>[O:1]=[C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][N:10]([CH2:22][CH2:23][C:24]3[CH:39]=[CH:38][C:27]4[O:28][CH2:29][C:30]5[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=5[C:32](=[O:33])[C:26]=4[CH:25]=3)[CH2:11][CH2:12]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 108064742-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethanol methanesulfonate

Product 1

HCID 134771164-(2-Keto-1-benzimidazolinyl)-1-[2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]piperidine

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5 g (0.023 m) of 4-(2-keto-1-benzimidazolinyl)piperidine, 7.65 g (0.023 m) of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethanol methanesulfonate of Example 1 and 3.17 g (0.023 m) of K2CO3 in 30 ml of absolute ethanol and 60 ml of methanol was refluxed overnight (about 16 hours). The reaction mixture was diluted with 800 ml of ethyl acetate, filtered and evaporated in vacuo. The residue was recrystallized from methanol to give after drying at 100° C. in vacuo, 5.78 g (56%) of 4-(2-keto-1-benzimidazolinyl)-1-[2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]piperidine, m.p. 116°-120° C.

Workup

  1. temperaturewas refluxed overnight (about 16 hours)
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customThe residue was recrystallized from methanol
  5. customto give
  6. dry with materialafter drying at 100° C. in vacuo, 5.78 g (56%) of 4-(2-keto-1-benzimidazolinyl)-1-[2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]piperidine, m.p. 116°-120° C.

Sources & evidence

ORD record
ord-8bc0a1f3a1e5491aaa011bfa6a14f5e8
Source dataset
uspto-grants-1988_06
Patent number
US04751238

Reaction notes

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