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

HRID 403128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403128
[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].[CH2:36](C1CCNCC1)C1C=CC=CC=1.C(OC1C=CC=CC=1CN(CC1C=CC=CN=1)CCCCl)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:19]([CH:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][N:9]([CH2:8][C:7]2[CH:32]=[CH:33][CH:34]=[CH:35][C:6]=2[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:14][CH2:15]1)[C:24]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:36]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 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 708963903-(4-benzylpiperidin-1-yl)-N-(2-tert-butoxybenzyl)-N-(pyridin-2-ylmethyl)propan-1-amineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The same procedure as described for compound 20 was applied to 4-benzyl piperidin (0.30 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). The residue was redissolved in CH2Cl2 and chromatographed on a silica-gel column with the following eluents: 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as yellow oil (64% yield). 1H NMR (CDCl3) δ 8.453 (dd, 1H, Ar), 7.576 (ddd, 1H, Ar), 7.516 (m, 2H, Ar), 7.224 (m, 2H, Ar), 7.135 (m, 1H, Ar), 7.075 (m, 4H, Ar), 6.982 (m, 2H, Ar), 3.730 (s, 2H, —CH2—), 3.655 (s, 2H, —CH2—), 2.864 (d, 2H, —CH2—), 2.482 (t, 4H, —CH2—CH2—), 2.324 (t, 2H, —CH2—), 1.888 (t, 2H, —CH2—), 1.728 (p, 2H, —CH2—), 1.586 (d, 2H, —CH2—), 1.502 (m, 1H, —CH—), 1.324 (s, 9H, —C(CH3)3), 1.288 (overlapped m, 2H, —CH2—). Mass Spec.=486.35 (M+H)+.

Aufarbeitung

  1. customchromatographed on a silica-gel column with the following eluents

Quellen und Nachweise

ORD-Eintrag
ord-d5602439f1e342639c0375fe25d43cc2
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08747810B2

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