Dicyclohexylcarbodiimide → 2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[4-(1H-indol-3-yl)butyl]acetamide

HRID 908935

Reaktionsgleichung

Reaktionsgleichung von HRID 908935
Cl.[CH3:2][N:3]([CH3:20])[C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8][C:7](=[CH:10][C:11]([OH:13])=O)[CH2:6][CH2:5]1.C1(N=[C:28]=[N:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:20][N:3]([CH3:2])[C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5][CH2:6][C:7](=[CH:10][C:11]([NH:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]2[C:31]3[C:30](=[CH:35][CH:34]=[CH:33][CH:32]=3)[NH:29][CH:28]=2)=[O:13])[CH2:8][CH2:9]1

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 67386703(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride

Produkt 1

HCID 116770742-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[4-(1H-indol-3-yl)butyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(4-dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride (592 mg, 2.0 mmol) in dry dimethylformamide (10 ml) under argon. The clear solution was cooled to 0° C. and dicyclohexylcarbodiimide (834 mg, 4.0 mmol) was added. The reaction mixture was stirred at RT for 4 d. Working up of the mixture was carried out by separating off the urea which had precipitated out and introducing the filtrate into a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml). Still further urea thereby precipitated out and was separated off. 5 M sodium hydroxide solution (5 ml, 25 mmol) was added to the aqueous phase and the mixture was diluted with water (300 ml) and stored at 5° C. for 16 h. The product thereby precipitated out as a colourless solid in a yield of 45% (387 mg) with an m.p. of 77-88° C.

Aufarbeitung

  1. customby separating off the urea which
  2. customhad precipitated out
  3. additionintroducing the filtrate
  4. additioninto a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml)
  5. customStill further urea thereby precipitated out and
  6. customwas separated off
  7. waitstored at 5° C. for 16 h
  8. customThe product thereby precipitated out as a colourless solid in a yield of 45% (387 mg) with an m.p. of 77-88° C.

Quellen und Nachweise

ORD-Eintrag
ord-cc05dd4208e2447b8baec14e16acdf78
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017630B2

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