Triethylamine → Trans-(+)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-1H-indole-1-acetamide

HRID 542215

Reaktionsgleichung

Reaktionsgleichung von HRID 542215
C(N(CC)CC)C.[N:8]1([CH2:17][C:18]([OH:20])=O)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.ClC(OCC)=O.[CH3:27][NH:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]1[N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>O1CCCC1>[CH3:27][N:28]([C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]1[N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)[C:18](=[O:20])[CH2:17][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 904481H-Indole-1-acetic acidHCID 13377463Cyclohexanamine, N-methyl-2-(1-pyrrolidinyl)-, trans-

Produkt 1

HCID 18607177Trans-(+)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-1H-indole-1-acetamideAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Triethylamine (139 μl, 1 mmol) was added to a solution of 1H-indole-1-acetic acid (175 mg, 1 mmol) in tetrahydrofuran (10 ml) at -15° C. with vigorous stirring. Ethyl chloroformate (96 μl, 1 mmol) was added, and the mixture stirred for five minutes. A solution of trans-(±)-N-methyl-2-(1-pyrrolidinyl)cyclohexanamine (182 mg, 1 mmol) in tetrahydrofuran (2 ml) was added, and stirring continued for 30 minutes at -15° C., then 30 minutes at room temperature. The reaction was evaporated to small volume, the residue dissolved in ethyl acetate (50 ml), and washed with saturated sodium biocarbonate solution (3×50 ml). The organic extract was drige (MgSO4), evaporated under reduced pressure, and recrystallized from diethyl ether/methylene chloride to yield the amide (100 mg, 32%); Vmax C=0 1635 cm-1.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 30 minutes at -15° C.
  3. custom30 minutes
  4. customat room temperature
  5. customThe reaction was evaporated to small volume
  6. dissolutionthe residue dissolved in ethyl acetate (50 ml)
  7. washwashed with saturated sodium biocarbonate solution (3×50 ml)
  8. extractionThe organic extract
  9. customevaporated under reduced pressure
  10. customrecrystallized from diethyl ether/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-b78c5c3004e445248105fe7e810969c9
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04656182

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