N,N-Dimethylethylenediamine → Benzyl 4-({[2-(dimethylamino)ethyl]amino}sulfonyl)-1-piperidinecarboxylate

HRID 516406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516406
Cl[S:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)(=[O:4])=[O:3].[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25]>C1COCC1>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH:25][S:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Komponenten

4

Edukt 2

HCID 66053N,N-DimethylethylenediamineHCID 21931260Benzyl 4-(chlorosulfonyl)piperidine-1-carboxylate

Produkt 1

HCID 66698082Benzyl 4-({[2-(dimethylamino)ethyl]amino}sulfonyl)-1-piperidinecarboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 430 mg (1.35 mmol) of benzyl 4-(chlorosulfonyl)-1-piperidinecarboxylate in 10 mL THF was treated with a 5-fold excess of N,N-dimethylethylenediamine and the mixture was stirred at room temperature for 2 hrs. The THF was removed under vacuum. After dilution with water, the product was extracted with CH2Cl2 and dried. Chromatography on alumina, eluting with EtOAc, gave 450 mg (90% yield) of benzyl 4-({[2-(dimethylamino)ethyl]amino}sulfonyl)-1-piperidinecarboxylate as an oil: 1H NMR (CDCl3) δ 7.40-7.30 (m, 5H), 5.13 (s, 2H), 4.33 (m, exchangeable with D2O, 1H), 3.16 (m, 2H), 3.04 (tt, J=11.9, 3.7 Hz, 1H), 2.81 (br t, J=11.9 Hz, 1H), 2.43 (m, 2H), 2.22 (s, 6H), 2.12 (br d, J=12.8 Hz, 2H), 1.74 (ddd, J=25.0, 12.6, 4.5 Hz, 2H).

Aufarbeitung

  1. customThe THF was removed under vacuum
  2. extractionAfter dilution with water, the product was extracted with CH2Cl2
  3. customdried
  4. washChromatography on alumina, eluting with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-a629bee584d74bba86271a7599e80b7b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108980B2

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