Benzyl Bromide → Tert-butyl 3-(benzylamino)benzylcarbamate

HRID 2071005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2071005
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(CC)CC>CN(C=O)C.O>[CH2:17]([NH:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 10775412tert-butyl N-((3-aminophenyl)methyl)carbamate

Produkt 1

HCID 68670447Tert-butyl 3-(benzylamino)benzylcarbamateAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred solution of the starting tert-butyl 3-aminobenzylcarbamate (0.925 g, 4.16 mmol, 1 eq, derived from 3-(aminomethyl)aniline (TCI America)) in 10 ml anhydrous DMF under Ar was treated with benzyl bromide (0.54 ml, 0.78 g, 4.58 mmol, 1.1 eq) and Et3N (0.75 ml, 0.55 g, 1.3 eq). After stirring for 48 h the reaction was diluted with water and extracted with EtOAc (×2). The combined organics were washed with water (×4), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.3937 g (1.26 mmol, 30% yield) of tert-butyl 3-(benzylamino)benzylcarbamate.

Aufarbeitung

  1. extractionextracted with EtOAc (×2)
  2. washThe combined organics were washed with water (×4), brine (×1)
  3. dry with materialdried over Na2SO4
  4. filtrationThe inorganics were filtered off
  5. customthe solvent was removed in vacuo
  6. customPurification via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5cae4fff012945eca2a35149b4a204f9
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299267B2

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