Dimethylformamide → 4-Amino-N-[1-(2-hydroxyethyl)-4-piperidinyl]-3-methoxybenzamide

HRID 1676523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676523
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][OH:10])[CH2:4][CH2:3]1.N1([O:20][C:21](=O)[C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[C:24]([O:29][CH3:30])[CH:23]=2)C2C=CC=CC=2N=N1.CN(C)C=O.C(N(CC)CC)C>ClCCl>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][OH:10])[CH2:4][CH2:3]2)=[O:20])=[CH:23][C:24]=1[O:29][CH3:30]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 106606854-Amino-3-methoxy-benzoic acid benzotriazol-1-yl esterHCID 157334452-(4-Aminopiperidin-1-yl)ethan-1-ol

Produkt 1

HCID 580150034-Amino-N-[1-(2-hydroxyethyl)-4-piperidinyl]-3-methoxybenzamideAusbeute 36,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 0.70 g (3.23 mmole) of 2-(4-amino-piperidin-1-yl)-ethanol, 0.92 g of 4-amino-3-methoxy-benzoic acid benzotriazol-1-yl ester, and 5 mL of dimethylformamide was added 1.63 g (16.1 mmole) of triethylamine. The mixture was stirred overnight, then taken up in 150 mL of dichloromethane and washed twice with saturated aqueous sodium bicarbonate, once with water, once with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-methanol (gradient, 100:0-80:20) to give 0.35 g of 4-amino-N-[1-(2-hydroxy-ethyl)-piperidin-4-yl]-3-methoxy-benzamide.

Aufarbeitung

  1. washwashed twice with saturated aqueous sodium bicarbonate, once with water, once with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with dichloromethane-methanol (gradient, 100:0-80:20)

Quellen und Nachweise

ORD-Eintrag
ord-56297c28c7b841c1ac7832fa7136d6c0
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003785B2

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