Potassium Carbonate → Tert-butyl 2-((3-(4-benzylpiperidin-1-yl)propyl)(2-tert-butoxybenzyl)amino)ethylcarbamate

HRID 403132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403132
[C:1]([O:5]C1C=CC=CC=1CN(CC1C=CC=CN=1)CCCN1CCC(C2C=CC=CC=2)CC1)([CH3:4])([CH3:3])[CH3:2].[CH2:36]([CH:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[C:49]([O:53][C:54]1[CH:74]=[CH:73][CH:72]=[CH:71][C:55]=1[CH2:56][N:57]([CH2:67][CH2:68][CH2:69]Cl)[CH2:58][CH2:59][NH:60][C:61](=[O:66])C(C)(C)C)([CH3:52])([CH3:51])[CH3:50].C([O-])([O-])=O.[K+].[K+]>>[CH2:36]([CH:43]1[CH2:48][CH2:47][N:46]([CH2:69][CH2:68][CH2:67][N:57]([CH2:56][C:55]2[CH:71]=[CH:72][CH:73]=[CH:74][C:54]=2[O:53][C:49]([CH3:50])([CH3:51])[CH3:52])[CH2:58][CH2:59][NH:60][C:61](=[O:66])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:45][CH2:44]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Komponenten

5

Edukt 4

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 67128436N-(2-((2-tert-butoxybenzyl)(3-chloropropyl)amino)ethyl)pivalamideHCID 70896369N-(2-tert-butoxybenzyl)-3-(4-phenylpiperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine

Produkt 1

HCID 70896359Tert-butyl 2-((3-(4-benzylpiperidin-1-yl)propyl)(2-tert-butoxybenzyl)amino)ethylcarbamateAusbeute 80 %

Versuchsvorschrift

The same procedure as described for compound 20 was applied to 4-benzylpiperidine (0.46 g, 2.63 mmol), compound 23 (0.7 g, 1.75 mmol), KI (0.87 g, 5.25 mmol) and K2CO3 (1.21 g, 8.75 mmol). The residue was purified on a silica gel TLC plate that was developed in 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as yellow oil (80% yield). 1H NMR (CDCl3) δ 7.373 (d, 1H, Ar), 7.264 (m, 2H, Ar), 7.176 (t, 1H, Ar), 7.137 (d, 2H, Ar), 7.137 (d, 2H, Ar), 7.108 (d, 1H, Ar), 7.021 (dd, 1H, Ar), 6.985 (t, 1H, Ar), 3.577 (s, 2H, —CH2—), 3.167 (d, 2H, —CH2—), 2.892 (d, 2H, —CH2—), 2.524 (d, 2H, —CH2—), 2.498 (t, 2H, —CH2—), 2.453 (t, 2H, —CH2—), 2.290 (t, 2H, —CH2—), 1.839 (t, 2H, —CH2—), 1.657 (m, 2H, —CH2—), 1.618 (d, 2H, —CH2—), 1.517 (m, 1H, —CH—), 1.426 (s, 9H, —C(CH3)3, 1.376 (s, 9H, —C(CH3)3, 1.329 (overlapped m, 4H). Mass Spec.=538.77 (M+H)+.

Aufarbeitung

  1. customThe residue was purified on a silica gel TLC plate that

Quellen und Nachweise

ORD-Eintrag
ord-e6466a842207460b93b3a12d7894ee7c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08747810B2

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