4-Methylmorpholine → N-[2-(4-Amino-phenyl)-1-phenyl-ethyl]-2,2-diphenyl-acetamide

HRID 1728357

Reaktionsgleichung

Reaktionsgleichung von HRID 1728357
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH2:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[C:17]1([CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24](O)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O>[C:10]1([CH:9]([NH:16][C:24](=[O:25])[CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 8333Diphenylacetic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 100590432-(4-Aminophenyl)-1-phenylethylamine

Produkt 1

HCID 9953161N-[2-(4-Amino-phenyl)-1-phenyl-ethyl]-2,2-diphenyl-acetamideAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(4-aminophenyl)-1-phenylethylamine (0.40 g, 1.9 mMol) and diphenylacetic acid (0.40 g, 1.9 mMol) were dissolved in dimethylformamide (DMF) (4 mL) at room temperature. To this was added HOBT (0.26 g, 1.9 mMol), NMM (0.19 g, 1.9 mMol) and EDCl (0.36 g) and the mixture was stirred at room temperature for 18 hours. The DMF was removed under vacuum and the oily residue was taken up in 100 mL ethyl acetate. The ethyl acetate was washed with saturated sodium bicarbonate and with brine, dried over magnesium sulfate, and evaporated to give 0.683 grams of a semi-solid. This was purified on 30 grams of flash-grade silica gel eluting with 100% dichloromethane to give 0.512 grams of the title compound, m.p. 161°-163° C.

Aufarbeitung

  1. customThe DMF was removed under vacuum
  2. washThe ethyl acetate was washed with saturated sodium bicarbonate and with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d5e76c5ba404472eb5335be1f6482264
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05326762

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