Hydrochloric Acid → 1'-Ethyl-5-(4'-hydrazinocarbonyl-2'-methylbiphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

HRID 1741125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741125
[CH2:1]([N:3]1[CH2:8][CH2:7][C:6]2([C:19]3[C:11](=[CH:12][C:13]4[CH2:14][CH2:15][N:16]([C:20]([C:22]5[CH:27]=[CH:26][C:25]([C:28]6[CH:33]=[CH:32][C:31]([C:34]7[O:35]C(C)=[N:37][N:38]=7)=[CH:30][C:29]=6[CH3:40])=[CH:24][CH:23]=5)=[O:21])[C:17]=4[CH:18]=3)[O:10][CH2:9]2)[CH2:5][CH2:4]1)[CH3:2].Cl.CCOCC>CO>[CH2:1]([N:3]1[CH2:8][CH2:7][C:6]2([C:19]3[C:11](=[CH:12][C:13]4[CH2:14][CH2:15][N:16]([C:20]([C:22]5[CH:23]=[CH:24][C:25]([C:28]6[CH:33]=[CH:32][C:31]([C:34]([NH:38][NH2:37])=[O:35])=[CH:30][C:29]=6[CH3:40])=[CH:26][CH:27]=5)=[O:21])[C:17]=4[CH:18]=3)[O:10][CH2:9]2)[CH2:5][CH2:4]1)[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 5311426SB-236057

Produkt 1

HCID 218337121'-Ethyl-5-(4'-hydrazinocarbonyl-2'-methylbiphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]Ausbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A stirred solution of 1'-ethyl-5-[2'-methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carbonyl]-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E26, 2.5 g, 4.7 mmole) in methanol (600 ml) was treated with 1M hydrogen chloride in ether (30 ml, 30 mmole) and kept at room temp. for 20 hours, then concentrated in vacuo. The residue was treated with 10% Na2CO3 solution (200 ml) and chloroform (500 ml), stirred well for 20 minutes, then the chloroform layer separated, dried and concentrated in vacuo. The residue was crystallised from ethyl acetate to afford the title compound as a beige solid (0.94 g, 39%) m.p. 222-225° C.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with 10% Na2CO3 solution (200 ml) and chloroform (500 ml)
  3. customthe chloroform layer separated
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-57fa90050dad4424a1f7118d76c56160
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972951

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