Hydrochloric Acid → 1-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperidine-4-carboxylic acid ethyl ester

HRID 907535

Reaktionsgleichung

Reaktionsgleichung von HRID 907535
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl:12][C:13]1[C:17](Cl)=[N:16][S:15][N:14]=1.Cl>CN(C=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:17]2[C:13]([Cl:12])=[N:14][S:15][N:16]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 70770Ethyl 4-piperidinecarboxylateHCID 798043,4-Dichloro-1,2,5-thiadiazole

Produkt 1

HCID 590139411-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperidine-4-carboxylic acid ethyl esterAusbeute 106,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Piperidine-4-carboxylic acid ethyl ester (14.0 mL, 91 mmol) was dissolved in DMF (15.0 mL) and heated to 100 C. 3,4-Dichloro-1,2,5-thiadiazole (4.0 mL, 42 mmol) was added and the mixture heated at 100 C. for 4 h. The reaction mixture was poured into 1N HCl and extracted with EtOAc (4×). The combined EtOAc extractions were washed with H2O (1×), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo to give 12.3 g (105%) of 1-(4-chloro-[1,2,5]thiadiazol-3-yl)-piperidine-4-carboxylic acid ethyl ester which was used without further purification. 1H NMR (CDCl3) 4.30-4.13 (m, 2H), 4.06-3.93 (m, 2H), 3.12-2.99 (m, 2H), 2.59 (m, 1H), 2.03 (m, 4H), 1.42-1.26 (m, (3H) ppm. LC-MS (MH+)=276.

Aufarbeitung

  1. temperatureheated to 100 C
  2. temperaturethe mixture heated at 100 C
  3. extractionextracted with EtOAc (4×)
  4. extractionThe combined EtOAc extractions
  5. washwere washed with H2O (1×), sat'd NaCl (1×)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c005bf9eda2847f994da754bc05b8427
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013156B2

Verknüpfte Notizen

Wird geladen…