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1,2-Dichloroethane → 1-(2-Methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)-piperazine-2-carboxamide

HRID 128588
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 128588
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:18])[CH3:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:19][C:20]([OH:22])=O.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH:32]([C:36]([NH2:38])=[O:37])[CH2:31]1.C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:11][CH2:12][N:13]([C:16](=[O:18])[CH3:17])[CH2:14][CH2:15]2)[CH:6]=[CH:5][C:4]=1[CH2:19][C:20]([N:33]1[CH2:34][CH2:35][N:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH3:23])[CH2:31][CH:32]1[C:36]([NH2:38])=[O:37])=[O:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 154305682-Carbamoyl-4-(2-methylphenyl)piperazineHCID 537598172-Methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetic acid

Produkt 1

HCID 536582201-(2-Methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)-piperazine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetic acid (35 mg, 0.11 mmol), 4-(2-methylphenyl)piperazine-2-carboxamide (25 mg, 0.11 mmol), EDC (28 mg, 0.15 mmol), and HBT (17 mg, 0.13 mmol) were combined in DMF (4 ml) under nitrogen. The mixture was rendered basic by addition of triethylamine (0.043 ml) and stirred at ambient temperature for 18 hours. The mixture was concentrated in vacuo and the residue was chromatographed on silica gel eluted with 2% methanol in methylene chloride. The combined product fractions were evaporated to dryness in vacuo and the residue was rechromatographed on silica gel eluted with 96:4:0.4 methylene chloride:methanol:concentrated ammonia. The combined product fractions were evaporated to dryness in vacuo and the residue was concentrated from methanol and ether to give 1-(2-methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)-piperazine-2-carboxamide.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was chromatographed on silica gel
  3. washeluted with 2% methanol in methylene chloride
  4. customThe combined product fractions were evaporated to dryness in vacuo
  5. customthe residue was rechromatographed on silica gel
  6. washeluted with 96:4:0.4 methylene chloride
  7. customThe combined product fractions were evaporated to dryness in vacuo
  8. concentrationthe residue was concentrated from methanol and ether

Quellen und Nachweise

ORD-Eintrag
ord-337256f47c4246ae986cc83b56554282
Quelldatensatz
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05464788

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