Ammonia → 2-(((2-Aminoethyl)(3-(4-benzylpiperidin-1-yl)propyl)amino)methyl)phenol

HRID 403134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403134
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35]C(C)(C)C)[CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N>CO>[NH2:20][CH2:19][CH2:18][N:17]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[OH:35])[CH2:16][CH2:15][CH2:14][N:11]1[CH2:10][CH2:9][CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

Komponenten

4

Edukt 2

HCID 222Ammonia2×HCID 70896359Tert-butyl 2-((3-(4-benzylpiperidin-1-yl)propyl)(2-tert-butoxybenzyl)amino)ethylcarbamate

Produkt 1

HCID 498501482-(((2-Aminoethyl)(3-(4-benzylpiperidin-1-yl)propyl)amino)methyl)phenolAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The same procedure as described for compound L24a was applied to compound 26 (0.7 g, 1.3 mmol) Purification was carried out on a silica gel TLC plate that was developed in with a 6% methanolic NH3 (7 M NH3 in methanol/94% CH2Cl2. The product was isolated as pale yellow oil (60%). 1H NMR (CDCl3) δ 7.257 (t, 2H, Ar), 7.163 (m, 2H, Ar), 7.118 (d, 2H, Ar), 6.952 (d, 1H, Ar), 6.801 (d, 1H, Ar), 6.757 (t, 1H, Ar), 3.724 (s, 2H, —CH2—), 2.867 (q, 4H, —CH2—CH—), 2.553 (m, 4H, —CH2—CH2—), 2.511 (d, 2H, —CH2—), 2.278 (t, 2H, —CH2—), 1.837 (ddd, 2H, —CH2—), 1.725 (p, 2H, —CH2—), 1.608 (d, 2H, —CH2—), 1.500 (m, 1H, —CH—), 1.275 (m, 2H, —CH2—). Mass Spec.=382.29 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-6aa25590264449dca6db770a4eecf32b
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08747810B2

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