Potassium Iodide → 4-(3-Morpholin-4-yl-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 2365186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2365186
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH2:18][CH2:19]Cl)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH2:18][CH2:19][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 227098904-tert-Butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine

Produkt 1

HCID 574939734-(3-Morpholin-4-yl-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-(3-Chloro-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (4.64 g), morpholine (1.6 mL, 1.3 eq.), potassium carbonate (2.17 g, 1.1 eq.), potassium iodide (1.11 g, 0.47 eq.) were refluxed together in dry MeCN (100 mL) overnight. Concentration in vacuo, then aqueous work-up followed by flash chromatography gave 4-(3-morpholin-4-yl-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (89%). Treatment with 2M HCl in ether gave product (4.46 g).

Aufarbeitung

  1. concentrationConcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2b27d9d7190849a5bf20cf239b5ae4cf
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697693B2

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