1-Bromo-3-chloropropane → N-(2-((2-tert-butoxybenzyl)(3-chloropropyl)amino)ethyl)pivalamide

HRID 403130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403130
[C:1]([O:5][C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[CH2:8][NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])OC(C)(C)C)([CH3:4])([CH3:3])[CH3:2].Br[CH2:25][CH2:26][CH2:27][Cl:28].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:1]([O:5][C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[CH2:8][N:9]([CH2:25][CH2:26][CH2:27][Cl:28])[CH2:10][CH2:11][NH:12][C:13](=[O:19])[C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 70896393Tert-butyl 2-(2-tert-butoxybenzylamino)ethylcarbamate

Produkt 1

HCID 67128436N-(2-((2-tert-butoxybenzyl)(3-chloropropyl)amino)ethyl)pivalamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Compound 14 (1 g, 4.1 mmol), 1-bromo-3-chloropropane (9.7 g, 60 mmol) and K2CO3 (0.56 g, 4.09 mmol) were added to 50 mL CH3CN, and the solution was stirred for 48 h. The solvent was evaporated to dryness and the residue was purified on a silica gel TLC plate that was developed in 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2 yield the desired product as a pale yellow oil (55%). 1H NMR (CDCl3) δ 7.341 (d, 1H, Ar), 7.139 (dd, 1H, Ar), 7.029 (m, 1H, Ar), 6.995 (m, 1H, Ar), 3.592 (s, 2H, —CH2—), 3.539 (t, 2H, —CH2—), 3.167 (m, 2H, —CH2—), 2.583 (ddd, 2H, —CH2—), 2.519 (ddd, 2H, —CH2—), 1.900 (p, 2H, —CH2—), 1.425 (s, 9H, —C(CH3)3), 1.385 (s, 9H, —C(CH3)3). Mass Spec.=399.96 (M+H)+.

Aufarbeitung

  1. customThe solvent was evaporated to dryness
  2. customthe residue was purified on a silica gel TLC plate that

Quellen und Nachweise

ORD-Eintrag
ord-e0053acbb5fc43889d63d0b42d38387f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08747810B2

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