Toluene → Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate

HRID 1091762Notizen

Reaktionsgleichung

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.Cl[CH2:19][C:20]([N:22]([CH3:24])[CH3:23])=[O:21].C1(C)C=CC=CC=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:23][N:22]([CH3:24])[C:20](=[O:21])[CH2:19][O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

Benzyl 4-hydroxypiperidine-1-carboxylate (5 g, 21.25 mmol), tetrabutylammonium hydrogensulfate (0.361 g, 1.06 mmol) and 2-chloro-N,N-dimethylacetamide (4.13 g, 27.63 mmol) were added to toluene (50 mL) to this was added sodium hydroxide (21 g, 210.02 mmol) in water (30 mL) and the reaction was stirred at 25° C. overnight. The reaction mixture was quenched with water (100 mL), extracted with Et2O (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford the desired compound as an orange liquid (6.00 g, 88% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.65-1.55 (2H, m), 1.93-1.86 (2H, m), 2.95 (3H, s), 3.03 (3H, s), 3.25-3.18 (2H, m), 3.63-3.57 (1H, m), 3.85-3.79 (2H, m), 4.17 (2H, s), 5.12 (2H, s), 7.38-7.30 (5H, m).

Aufarbeitung

customThe reaction mixture was quenched with water (100 mL)
extractionextracted with Et2O (3×75 mL)
dry with materialthe organic layer was dried over MgSO4
filtrationfiltered
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-e753dd91363d42ad809fdc46c4ef484c
Quelldatensatz: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08129380B2

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