Acetic Acid → N-benzyl4-(N-Boc-2-aminoethyl)aniline

HRID 51287

Reaktionsgleichung

[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC(O)=O.[BH3-]C#N.[Na+]>C1(C)C=CC=CC=1.CO>[CH2:18]([NH:15][C:14]1[CH:16]=[CH:17][C:11]([CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])=[CH:12][CH:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

A mixture of 4-(N-Boc-2-aminoethyl)aniline 28 (10 g, 42.34 mmole), benzaldehyde (4.52 mL, 44.47 mmole), and molecular sieves 4A (10 g) in toluene (100 mL) was refluxed at 95° C. for 15 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give a colorless oil. The oil was dissolved in MeOH (150 mL) and AcOH (0.5 mL) and NaCNBH3 (2.79 g, 44.4 mmole) were added. The reaction mixture was stirred at 0° C. for 1 h and at rt for 2 h and then concentrated in vacuo to give a pale yellow oily residue. Purification by flash silica column chromatography: 1/1 hexane/EtOAc gave N-benzyl4-(N-Boc-2-aminoethyl)aniline 41 as colorless oil (11.5 g, 83%). Rf=0.75 in 1/1 hexane/EtOAc. H1-NMR (CD3OD, 299.96 MHz): δ (ppm) 7.38-7.2 (m, 5H), 6.87-6.87-6.84 (d, 2H), 6.58-6.55 (d, 2H), 4.27 (s, 2H), 3.2-3.15 (m, 2H), 2.6-2.56 (t, 2H), 1.41 (s, 9H); ESMS (C20H26N2O2): calcd. 326.4, obsd. 328 [M+H]+.

Aufarbeitung

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customto give a colorless oil
concentrationconcentrated in vacuo
customto give a pale yellow oily residue
customPurification by flash silica column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-9cd98278dcef46f0869f5af98e127f68
Quelldatensatz: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06713651B1

Verknüpfte Notizen

Wird geladen…