Potassium Carbonate → N-(2-tert-butoxybenzyl)-3-(4-(2-methoxyphenyl)piperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine

HRID 403127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403127
[C:1]([O:5][C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[CH2:8][N:9]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][O:37]C1(C2C=CC=CC=2)CCCCN1.C(OC1C=CC=CC=1CN(CC1C=CC=CN=1)CCCCl)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>>[C:1]([O:5][C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[CH2:8][N:9]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=2[O:37][CH3:36])[CH2:17][CH2:18]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 4

HCID 11430Potassium CarbonateHCID 671284982-Methoxy-2-phenylpiperidinHCID 67128530N-(2-tert-butoxybenzyl)-3-chloro-N-(pyridin-2-ylmethyl)propan-1-amineHCID 70896369N-(2-tert-butoxybenzyl)-3-(4-phenylpiperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine

Produkt 1

HCID 67128412N-(2-tert-butoxybenzyl)-3-(4-(2-methoxyphenyl)piperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amineAusbeute 59 %

Versuchsvorschrift

The same procedure as described for compound 20 was applied to 2-methoxy-2-phenylpiperidin (0.33 g, 1.73 mmol), compound 19 (0.4 g, 1.15 mmol), KI (0.57 g, 3.45 mmol) and K2CO3 (0.79 g, 5.75 mmol). Purification was carried out on a silica gel TLC plate that was developed in with a 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as pale yellow oil (59%). 1H NMR (CDCl3) δ 8.486 (m, 1H, Ar), 7.591 (m, 3H, Ar), 7.22 (dd, 1H, Ar), 7.135 (m, 3H, Ar), 7.017 (dd, 2H, Ar), 6.901 (dd, 1H, Ar), 6.819 (d, 1H, Ar), 3.781 (s, 3H, —OCH3), 3.764, (s, 2H, —CH2—), 3.691 (s, 2H, —CH2—), 3.002 (d, 2H, —CH2—), 2.939 (m, 1H, —CH—), 2.521 (t, 2H, —CH2—), 2.373 (t, 2H, —CH2—), 2.053 (m, 3H, —CH—CH2—), 1.769 (m, 6H), 1.354 (s, 9H, —C(CH3)3). Mass Spec.=502.34 (M+H)+.

Aufarbeitung

  1. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-0f646aae26c14e71aab6de363e067703
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08747810B2

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