1,1'-Carbonyldiimidazole → 4-Cyano-4'-[[(3-ethoxycarbonylpiperidino)carbonyl]methyloxy]biphenyl

HRID 1598400

Reaktionsgleichung

Reaktionsgleichung von HRID 1598400
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)([OH:15])=O.[NH:32]1[CH2:37][CH2:36][CH2:35][CH:34]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:33]1>O1CCCC1>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][CH2:16][C:13]([N:32]3[CH2:37][CH2:36][CH2:35][CH:34]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:33]3)=[O:15])=[CH:19][CH:20]=2)=[CH:25][CH:26]=1)#[N:31]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 98969Ethyl nipecotateHCID 432431004-(Carboxymethyloxy)-4'-cyano-biphenyl

Produkt 1

HCID 538027554-Cyano-4'-[[(3-ethoxycarbonylpiperidino)carbonyl]methyloxy]biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5.35 g of carbonyldiimidazole are added to a solution of 7.6 g of 4-(carboxymethyloxy)-4'-cyano-biphenyl (prepared from 4-cyano-4'-hydroxy-biphenyl and tert.butyl bromoacetate according to Example 13, but with potassium tert.butoxide as base, and subsequent ester cleaving with trifluoroacetic acid) in 30 ml of tetrahydrofuran and the resulting mixture is stirred for 0.5 hours at ambient temperature. 5.1 ml of ethyl piperidine-3-carboxylate are added and the mixture is stirred for 22 hours at ambient temperature. The tetrahydrofuran is evaporated off, the residue is taken up in ethyl acetate and washed successively with saturated sodium bicarbonate solution, 0.1N hydrochloric acid and water. After evaporation of the organic phase the residue remains as an oil.

Aufarbeitung

  1. stirringthe mixture is stirred for 22 hours at ambient temperature
  2. customThe tetrahydrofuran is evaporated off
  3. washwashed successively with saturated sodium bicarbonate solution, 0.1N hydrochloric acid and water
  4. customAfter evaporation of the organic phase the residue

Quellen und Nachweise

ORD-Eintrag
ord-0f276910d0954b58838aa61dd9ec8778
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05736559

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