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 1741125Notes

Reaction equation

HRID 1741125 reaction equation
[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]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 5311426SB-236057

Product 1

HCID 218337121'-Ethyl-5-(4'-hydrazinocarbonyl-2'-methylbiphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]Yield 39.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-57fa90050dad4424a1f7118d76c56160
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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