Methyl iodide → tert-Butyl 4-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

HRID 962741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 962741
[H-].[Na+].I[CH3:4].[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[NH:20][C:19]2=[O:27])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>CN(C=O)C>[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]([CH3:4])[C:19]2=[O:27])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13046891tert-Butyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 21222103tert-Butyl 4-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 0.060 g of sodium hydride, 60% oil dispersion, 10 mL of DMF, 0.086 mL of iodomethane, and 0.4 g of 1,3-dihydro-1-(1-tert-butyloxycarbonylpiperidin-4-yl)-2H-benzimidazol-2-one was stirred for 12 h, then partitioned between 100 mL of chloroform and 50 mL of water. The chloroform extracts dried over MgSO4, and concentrated under reduced pressure. Trituration with hexane gave 0.38 g of 1,3-dihydro-1-(1-tert-butyloxycarbonylpiperidin-4-yl)-3-methyl-2H-benzimidazol-2-one as a crystalline solid: 1H NMR (300 MHz, CDCl3) 7.13-7.03 (m, 3H), 6.98 (d, 1H), 4.5 (m, 1H), 4.3 (br m, 2H), 3.4 (s, 3H), 2.85 (m, 4H), 2.3 (m, 2H), 1.8 (d, 2H), 1.5 (s, 91H).

Aufarbeitung

  1. custompartitioned between 100 mL of chloroform and 50 mL of water
  2. dry with materialThe chloroform extracts dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5aa7e6141d854d6394d1a1d912291f29
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760054

Notizen zur Reaktion

Wird geladen…