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

HRID 609737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 609737
N[CH:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][CH2:3]1.NC1CCC(C2C=C3C(=CC=2)NC=C3CCN2CCCC2)(O)CC1.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl.C1COCC1.C(OCC)(=O)C.C(Cl)(Cl)Cl>[C:5]1([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:6][CH2:7][CH2:2][CH2:3][CH:4]=1

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 699483875-(1-aza-1-methyl-4-hydroxycyclohex-4-yl)-3-(2-pyrrolidinylethyl)-1H-indoleHCID 699493865-(1-Aza-1-methylcyclohex-3-en-4-yl)-3-(2-pyrrolidinylethyl)-1H-indole

Produkt 1

HCID 699489945-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-(1-Aza-1-methylcyclohex-3-en-4-yl)-3-(2-pyrrolidinylethyl)-1H-indole: (17.6 mg, 13%) from 5-(1-aza-1-methyl-4-hydroxycyclohex-4-yl)-3-(2-pyrrolidinylethyl)-1H-indole (Example 13d, 145 mg, 0.44 mmol), triethylamine (0.95 mL, 6.8 mmol) and MsCl (0.25 mL, 3.2 mmol) in dichloromethane (3.5 mL) and THF (7 mL) with the exception that the reaction was carried out at a gentle reflux overnight and the extraction solvent consisted of a mixture of dichloromethane, chloroform, and ethyl acetate. Starting material (17 mg) was also recovered. The product in this case was converted to the hydrochloride salt which was soluble in methanol; HRMS-FAB+ for C20H27N3 : calculated MH+ :310.22833; found MH+ :310.22650.

Aufarbeitung

  1. temperaturea gentle reflux overnight
  2. customStarting material (17 mg) was also recovered

Quellen und Nachweise

ORD-Eintrag
ord-4b3470229f6b48aea2f2e470c5a51fd0
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998438

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