Tetrahydrofuran → N-[(2-bromophenyl)methyl]cyclopropanamine

HRID 1631153

Reaktionsgleichung

Reaktionsgleichung von HRID 1631153
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.O1CCCC1.[CH:15]1([NH2:18])[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O.C(O)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:18][CH:15]1[CH2:17][CH2:16]1

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 69828CyclopropylamineHCID 811292-BromobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 20120601N-[(2-bromophenyl)methyl]cyclopropanamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1 ml of 2-bromobenzaldehyde are dissolved in 20 ml of 1,2-dichloroethane and ml of tetrahydrofuran. 799 μl of cyclopropylamine and 643 μl of glacial acetic acid are added, and the mixture is stirred at 60° C. for 6 h. After cooling to 25° C., 5.3 g of sodium triacetoxyborohydride are added and stirred at 25° C. for a further 12 h. The mixture is poured into water, extracted three times with dichloromethane, and the combined organic phases are dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness and purified by chromatography (reversed phase HPLC).

Aufarbeitung

  1. temperatureAfter cooling to 25° C.
  2. stirringstirred at 25° C. for a further 12 h
  3. extractionextracted three times with dichloromethane
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate is evaporated to dryness
  7. custompurified by chromatography (reversed phase HPLC)

Quellen und Nachweise

ORD-Eintrag
ord-1d3450ae3bd44f089cabb5d6c30401eb
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791129B2

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