Dimethylamine → Benzyl 4-[(dimethylamino)sulfonyl]-1-piperidinecarboxylate

HRID 1619872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619872
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][NH:22][CH3:23]>C1COCC1>[CH3:21][N:22]([CH3:23])[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 674DimethylamineHCID 21931260Benzyl 4-(chlorosulfonyl)piperidine-1-carboxylate

Produkt 1

HCID 53587548Benzyl 4-[(dimethylamino)sulfonyl]-1-piperidinecarboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 190 mg (0.6 mmol) of benzyl 4-(chlorosulfonyl)-1-piperidinecarboxylate in 10 mL THF was treated with a 10-fold excess of 40% aq. dimethylamine and the mixture was stirred at room temperature for 2 hrs. The THF was removed under vacuum. The residue was diluted with water, extracted with CH2Cl2, and dried. Chromatography on alumina, eluting with CH2Cl2, gave 175 mg (89% yield) of benzyl 4-[(dimethylamino)sulfonyl]-1-piperidinecarboxylate as an oil: 1H NMR (CDCl3) δ 7.40-7.30 (m, 5H), 5.13 (s, 2H), 4.31 (m, 2H), 3.10 (tt, J=12.0, 3.7 Hz, 1H), 2.92 (s, 6H), 2.85-2.75 (m, 2H), 2.04 (br d, J=13.7 Hz, 2H), 1.76 (dq, J=12.6, 4.5 Hz, 2H).

Aufarbeitung

  1. customThe THF was removed under vacuum
  2. additionThe residue was diluted with water
  3. extractionextracted with CH2Cl2
  4. customdried
  5. washChromatography on alumina, eluting with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-da34cd06ebd54c7a92079867e73eeb67
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772287B2

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