Hydrochloric Acid → benzyl N-[4-(2-aminoethyl)piperidine-1-carboximidoyl]carbamate

HRID 1585486

Reaktionsgleichung

Reaktionsgleichung von HRID 1585486
[BH4-].[Na+].[N:3]([CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[NH:26])[NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:10][CH2:9]1)=[N+]=[N-].Cl>O.O1CCCC1.[Pd]>[NH2:3][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[NH:26])[NH:15][C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:10][CH2:9]1

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 140379074benzyl N-[4-(2-azidoethyl)piperidine-1-carboximidoyl]carbamate

Produkt 1

HCID 140379088benzyl N-[4-(2-aminoethyl)piperidine-1-carboximidoyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysator2×HCID 962WaterLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 30 ml of water was added 0.40 g of 10% Pd/C. Sodium borohydride, 1.0 g (0.031 mol), was dissolved in 30 ml of water and was added carefully to the stirred and ice-cooled slurry of Pd/C and water. 4-Azidoethyl-1-benzyloxycarbonylamidino piperidine, 2.9 g (8.8 mmol), was dissolved in 50 ml of tetrahydrofurane and this solution was added dropwise to the ice-cooled aqueous slurry above. After 4 h of stirring at room temperature the mixture was ice-cooled again and 30 ml of 2 M HCl was added. The mixture was filtered through celite and the celite was rinsed with additional water. The tetrahydrofuran was evaporated and the aqueous phase was washed with ethyl acetate. The aqueous phase was made alkaline with 2 M NaOH and extracted with methylene chloride three times. The combined organic phase was washed with water, dried (Na2SO4) and evaporated. The product was used in the following step without further purification.

Aufarbeitung

  1. additionwas added carefully to the
  2. temperaturecooled aqueous slurry above
  3. stirringAfter 4 h of stirring at room temperature the mixture
  4. temperaturecooled again
  5. filtrationThe mixture was filtered through celite
  6. washthe celite was rinsed with additional water
  7. customThe tetrahydrofuran was evaporated
  8. washthe aqueous phase was washed with ethyl acetate
  9. extractionextracted with methylene chloride three times
  10. washThe combined organic phase was washed with water
  11. dry with materialdried (Na2SO4)
  12. customevaporated
  13. customThe product was used in the following step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-c9ea68e79135416aae8f444fb3b33d2c
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05939392

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