Water → 1-(5-Bromopyridin-2-yl)-4-cyclopropylpiperazine

HRID 1887151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887151
C(O[C:4]1(O[Si](C)(C)C)[CH2:6][CH2:5]1)C.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[N:17][CH:18]=1.O.[BH3-]C#N.[Na+]>C1COCC1.C(O)(=O)C>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:20][CH2:21][N:22]([CH:4]3[CH2:5][CH2:6]3)[CH2:23][CH2:24]2)=[N:17][CH:18]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 164142271-(5-Bromopyridin-2-yl)piperazine

Produkt 1

HCID 231545451-(5-Bromopyridin-2-yl)-4-cyclopropylpiperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

[(1-Ethoxy-cyclopropyl)oxy]trimethylsilane (26 mL, 129.3 mmol) was added to a solution of 1-(5-bromopyridin-2-yl)-piperazine (15 g, 62.0 mmol) in THF (120 mL). Water (24 mL), acetic acid (11 mL), and 1 M NaCNBH3 in THF (90 mL, 90 mmol) were added to the reaction mixture, which was then heated at reflux temperature for 3 hours. The resulting solution was cooled to rt and evaporated to dryness in vacuo. The residue was dissolved in a mixture of dichloromethane (200 mL) and water (50 mL) and 4 N sodium hydroxide (20 mL) was added to pH 8-9. The organic phase was isolated and the aqueous phase was extracted with further dichloromethane (100 mL). The combined organic phases were evaporated to dryness in vacuo and the residue was purified on a silica gel column (gradient: from 5% ethyl acetate in heptane to 100% ethyl acetate over 40 min.). This afforded 13.1 g (75%) of 1-(5-bromopyridin-2-yl)-4-cyclopropylpiperazine.

Aufarbeitung

  1. temperaturewas then heated
  2. temperatureat reflux temperature for 3 hours
  3. customevaporated to dryness in vacuo
  4. dissolutionThe residue was dissolved in a mixture of dichloromethane (200 mL) and water (50 mL) and 4 N sodium hydroxide (20 mL)
  5. additionwas added to pH 8-9
  6. customThe organic phase was isolated
  7. extractionthe aqueous phase was extracted with further dichloromethane (100 mL)
  8. customThe combined organic phases were evaporated to dryness in vacuo
  9. customthe residue was purified on a silica gel column (gradient: from 5% ethyl acetate in heptane to 100% ethyl acetate over 40 min.)

Quellen und Nachweise

ORD-Eintrag
ord-7a14420229f24138a5da0ec82779a23f
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501739B2

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