1-Isocyanato-4-methoxybenzene → N-(4-Methoxyphenyl)-N'-[3-(3-piperidinomethylphenoxy)propyl]urea

HRID 1710042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710042
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>C(O)C>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:15][CH2:14][CH2:13][CH2:12][O:11][C:10]2[CH:16]=[CH:17][CH:18]=[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:9]=2)=[O:29])=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Produkt 1

HCID 14514731N-(4-Methoxyphenyl)-N'-[3-(3-piperidinomethylphenoxy)propyl]ureaAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To the mixture of 3-(3-piperidinomethylphenoxy)propylamine (3.1 g) in ethanol (31 ml) was added 4-methoxyphenylisocyanate (1.9 g) dropwise slowly under cooling on an ice-water bath. The reaction mixture was stirred at room temperature for 2.5 hours and then concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane (50 ml), washed with diluted hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution successively and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the crude product (3.3 g) was obtained (yield 66.0 %). This crude product was recrystallized from ethanol to give the title compound (2.1 g), mp 111°-112° C.

Aufarbeitung

  1. temperatureunder cooling on an ice-water bath
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in dichloromethane (50 ml)
  4. washwashed with diluted hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of the solvent under reduced pressure
  7. customthe crude product (3.3 g) was obtained (yield 66.0 %)
  8. customThis crude product was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2a59726b256447c5b6dcebbecc60bab1
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04952591

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