Piperidine-1-propylamine → N-(1-Methylethyl)-N-[2-(phenylsulfonyl)ethyl]-N'-[3-(1-piperidinyl)propyl]urea

HRID 4222

Reaktionsgleichung

Reaktionsgleichung von HRID 4222
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[C:23]1([S:29]([CH2:32][CH2:33][NH:34][CH:35]([CH3:37])[CH3:36])(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH3:36][CH:35]([N:34]([CH2:33][CH2:32][S:29]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:30])=[O:31])[C:1]([NH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:2])[CH3:37]

Komponenten

5

Edukt 3

HCID 19049Piperidine-1-propylamineHCID 682631,1'-CarbonyldiimidazoleHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamine

Produkt 1

HCID 20152828N-(1-Methylethyl)-N-[2-(phenylsulfonyl)ethyl]-N'-[3-(1-piperidinyl)propyl]ureaAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 5.16 g (0.0319 mole) of 1,1'-carbonyldiimidazole and 4.16 g (0.029 mole) of N-(3-aminopropyl)piperidine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 6.13 g (0.027 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the mixture was refluxed for 20 hr. The solvent was removed in vacuo, and the residue was dissolved in a 60/40 mixture of ether and methylene chloride, respectively. The solution was extracted with three portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (chloroform and methanol, gradiently eluted with methanol up to 10% methanol) gave 2.89 g (27.1%) of oil:

Aufarbeitung

  1. temperaturethe mixture was refluxed for 20 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in a 60/40 mixture of ether and methylene chloride
  4. extractionThe solution was extracted with three portions of water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customto give an oil
  8. washFlash chromatography on silica gel (chloroform and methanol, gradiently eluted with methanol up to 10% methanol)

Quellen und Nachweise

ORD-Eintrag
ord-f9350ef6ad3d4d59a6d8bded0cf293e3
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04724235

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