Ethanesulfonylchloride, 2-chloro- → 1-(2-Methoxy-4-(1-ethenylsulfonyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

HRID 128594

Reaktionsgleichung

Reaktionsgleichung von HRID 128594
Cl[CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].Cl.Cl.[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:15]=[CH:14][C:13]=1[CH2:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])[CH2:30][CH:29]1[C:41]([NH2:43])=[O:42])=[O:27].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([S:4]([CH:3]=[CH2:2])(=[O:6])=[O:5])[CH2:21][CH2:20]2)[CH:15]=[CH:14][C:13]=1[CH2:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])[CH2:30][CH:29]1[C:41]([NH2:43])=[O:42])=[O:27]

Komponenten

5

Edukt 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 81531DiisopropylethylamineHCID 676564691-(2-Methoxy-4-(4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide dihydrochloride

Produkt 1

HCID 189141631-(2-Methoxy-4-(1-ethenylsulfonyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-Chloroethanesulfonyl chloride (0.035 ml, 54.6 mg, 0.33 mmol) in methylene chloride (3 ml) was cooled in an ice bath under nitrogen. A solution of 1-(2-methoxy-4-(4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)-piperazine-2-carboxamide dihydrochloride (149 mg, 0.28 mmol) and diisopropylethylamine (0.243 ml, 0.18 g, 1.4 mmol) in methylene chloride (3 ml) was added dropwise and the mixture was stirred in the cold for 18 hours. The mixture was concentrated in vacuo and the residue chromatographed on silica gel eluted with 3% methanol in methylene chloride. The combined product fractions were evaporated to dryness in vacuo to give 1-(2-methoxy-4-(1-ethenylsulfonyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue chromatographed on silica gel
  3. washeluted with 3% methanol in methylene chloride
  4. customThe combined product fractions were evaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-377d1b3ed3b348be93c0c1e64baff28d
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464788

Verknüpfte Notizen

Wird geladen…