2-Thiophenecarbonyl chloride → Tert-butyl 4-(thiophene-2-carbonyl)piperazine-1-carboxylate

HRID 14356

Reaktionsgleichung

Reaktionsgleichung von HRID 14356
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Komponenten

5

Edukt 2

HCID 789282-Thiophenecarbonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 2796164Tert-butyl 4-(thiophene-2-carbonyl)piperazine-1-carboxylateAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

2-Thiophenecarbonylchloride (2.04 g, 1.49 mL) was added to a solution of tert-butyl-1-piperazinecarboxylate (2.5 g, 13.4 mmol) and DMAP (20 mg) in pyridine (15 mL) at 0° C. under N2 atmosphere and stirred at room temperature for overnight. The mixture was poured into ice water, the precipitate was filtered, washed several times with water, and dried to yield white solids (3.5 g, 88%). Mp 76° C. 1H NMR (DMSO-d6): δ 1.42 (s, 12H), 3.40 (m, 4H), 3.61 (m, 4H), 7.12 (m, 1H), 7.43 (d, J=4.1 Hz, 1H), 7.77 (d, J=4.8 Hz, 1H). EIMS m/z 297 (M+1), 319 (M+23). Anal. (C14H20N2O3S) C, H, N.

Aufarbeitung

  1. filtrationthe precipitate was filtered
  2. washwashed several times with water
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2f59057de17345809ee82ef0e8995252
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732146B2

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