1-Bromo-3-chloropropane → N-(2-tert-butoxybenzyl)-3-chloro-N-(pyridin-2-ylmethyl)propan-1-amine

HRID 403125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403125
[C:1]([O:5][C:6]1[CH:20]=[CH:19][CH:18]=[CH:17][C:7]=1[CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][CH2:23][CH2:24][Cl:25].C([O-])([O-])=O.[K+].[K+]>>[C:1]([O:5][C:6]1[CH:20]=[CH:19][CH:18]=[CH:17][C:7]=1[CH2:8][N:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH2:22][CH2:23][CH2:24][Cl:25])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 70896659N-(2-tert-butoxybenzyl)-1-(pyridin-2-yl)methanamine

Produkt 1

HCID 67128530N-(2-tert-butoxybenzyl)-3-chloro-N-(pyridin-2-ylmethyl)propan-1-amine

Versuchsvorschrift

Compound 19 was synthesized with 9 (0.9 g, 3.32 mmol), using 1-bromo-3-chloropropane (10.5 g, 66 mmol) and K2CO3 (0.46 g, 3.32 mmol) following a procedure analogous to that described above for 10. Purification was carried out on a silica-gel column with the following eluents: First with 100% CH2Cl2 and then 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2. The product was isolated as pale yellow oil (65%). 1H NMR (CDCl3) δ 8.491 (m, 1H, Ar), 7.624 (m, 1H, Ar), 7.512 (t, 1H, Ar), 7.111 (m, 2H, Ar), 7.010 (m, 2H, Ar), 3.750 (s, 2H, —CH2—), 3.690 (s, 2H, —CH2—), 3.513 (ddd, 2H, —CH2—), 2.616 (t, 2H, —CH2—), 1.946 (m, 2H, —CH2—), 1.354 (s, 9H, —C(CH3)3). Mass Spec.=346.89 (M+H)+.

Aufarbeitung

  1. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-1dd882d0a72d44769a0f2b4def352e38
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08747810B2

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