N,N-Diphenylcarbamic chloride → N-{4-[1-(diphenylaminocarbonyl)-piperidin-4-yl]-butyl}-3-(pyridin-3-yl)-acrylamide

HRID 1294457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1294457
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:23])[CH:15]=[CH:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:5][CH2:4]1.[C:24]1([N:30]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:31](Cl)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[C:24]1([N:30]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:31]([N:3]2[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:23])[CH:15]=[CH:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:5][CH2:4]2)=[O:32])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

4

Edukt 2

HCID 65741N,N-Diphenylcarbamic chlorideHCID 69451641N-[4-(piperidine-4-yl)butyl]-3-(pyridin-3-yl)-acrylamide Dihydrochloride

Produkt 1

HCID 54512164N-{4-[1-(diphenylaminocarbonyl)-piperidin-4-yl]-butyl}-3-(pyridin-3-yl)-acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

6.5 g (18.0 mmol) N-[4-(piperidin-4-yl)-butyl]-3-(pyridin-3-yl)-acrylamide dihydrochloride (K22.142) and 5.77 ml (41.4 mmol) TEA are placed in 70 ml abs. dichlormethane and cooled to ca. 0° C. under moisture exclusion. 4.58 g (19.8 mmol) N,N-diphenylcarbamic acid chloride are dissolved in 20 ml abs. dichlormethane and added dropwise. The mixture is stirred at RT overnight without further cooling. 4 ml (28.7 mmol) TEA are added and the red colored suspension is stirred a further 2 hours at RT. Subsequently, the batch is washed with 80 ml water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH (98/2) and crystallized twice, each from 60 ml acetic acid ethyl ester, after drawing off the solvent. Beige colored crystals with a MP of 132–134° C.; yield: 5.3 g (60%).

Aufarbeitung

  1. stirringthe red colored suspension is stirred a further 2 hours at RT
  2. washSubsequently, the batch is washed with 80 ml water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent is removed under vacuum
  5. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH (98/2)
  6. customcrystallized twice

Quellen und Nachweise

ORD-Eintrag
ord-7edef60d61794824ba13c9089cda8d2f
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241745B2

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