Sodium Chloride → tert-Butyl 4-(3-bromopropyl)piperidine-1-carboxylate

HRID 881024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 881024
O[CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Na+]>C(OCC)(=O)C.O.O1CCCC1>[Br:19][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

Produkt 1

HCID 18409081tert-Butyl 4-(3-bromopropyl)piperidine-1-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a tetrahydrofuran (110 mL) solution of 10.7 g of tert-butyl 4-(3-hydroxypropyl)-1-piperidinecarboxylate was added 19.0 g of carbon tetrabromide under cooling with water, to which 15.0 g of triphenylphosphine was then added over a period of 13 minutes. This mixture was stirred at room temperature for 2 hours and 30 minutes and allowed to stand for 13 hours. To the reaction mixture were added water, ethyl acetate, and a saturated sodium chloride aqueous solution. The organic layer was separated, washed with a saturated sodium chloride aqueous solution, and dried with anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; hexane:ethyl acetate=3:1) to provide 13.2 g of tert-butyl 4-(3-bromopropyl)-1-piperidinecarboxylate as colorless oily form.

Aufarbeitung

  1. additionwas then added over a period of 13 minutes
  2. waitto stand for 13 hours
  3. customThe organic layer was separated
  4. washwashed with a saturated sodium chloride aqueous solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe resultant residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-e13abaa26faa4db3bcea077b5cd40093
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993603B2

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