Triethylamine → 5-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole

HRID 609736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 609736
CS(Cl)(=O)=O.O[C:7]1([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[C:16]3[CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C>ClCCl>[NH3:18].[C:7]1([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[C:16]3[CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 699487065-(1-hydroxycyclohex-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole

Produkt 2

HCID 222AmmoniaAusbeute 5 %HCID 699489945-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indoleAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Methanesulfonyl chloride (0.042 mL, 0.54 mmol) was added to a solution of 5-(1-hydroxycyclohex-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole (Example 13a, 50.6 mg, 0.16 mmol) and triethylamine (0.15 mL, 1.06 mmol) in dichloromethane (2.5 mL) at 0° C. The reaction was allowed to warm slowly to room temperature and stirring was continued overnight. The reaction mixture was diluted with dichloromethane (100 mL) and washed sequentially with water and brine, dried over sodium sulfate and the solvent was removed in vacuo. Flash chromatography (silica, 5-8% 2M methanolic ammonia in dichloromethane) yielded 5-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole (21.8 mg, 46%); HRMS-FAB+ for C20H26N2 :calculated MH+ :295.21744; found MH+ :295.21953.

Aufarbeitung

  1. washwashed sequentially with water and brine
  2. dry with materialdried over sodium sulfate
  3. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1ef81c29f2d24351ac8876be0312f581
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998438

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