Hydrazine → 2-Hydrazinyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine

HRID 2406132

Reaktionsgleichung

Reaktionsgleichung von HRID 2406132
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[NH2:14][NH2:15]>N1C=CC=CC=1>[NH:14]([C:2]1[N:3]=[CH:4][C:5]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1)[NH2:15]

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 581995242-Chloro-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine

Produkt 1

HCID 552819292-Hydrazinyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

2-Chloro-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine (1.5 g) was treated with anhydrous pyridine (15 mL) and anhydrous hydrazine (7 mL) at 120° C. for 3.75 h. The solvent was removed under vacuum. The residue was partitioned between chloroform and 1M aqueous potassium carbonate solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 2-hydrazinyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine as a beige solid, 1.28 g; 1H NMR (CDCl3, 300 MHz) 8.00 (s, 1H), 6.63 (br s, 1H), 3.93 (br s, 2H), 2.76 (m, 2H), 2.60 (m, 2H), 1.74 (m, 2H), 1.63 (m, 2H), 1.40 (m, 4H) ppm; 13C NMR (CDCl3, 75 MHz) 170.57, 163.81, 157.22, 124.14, 34.31, 32.65, 30.24, 28.66, 26.32, 26.08; MS (ES) 193 (M+H).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customThe residue was partitioned between chloroform and 1M aqueous potassium carbonate solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1be71c0455ec464daaa0e0130f213446
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809347B2

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