Potassium Carbonate → 2-((2(RS)-(Phenoxymethyl)morpholin-4-yl)methyl)benzimidazole

HRID 977081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 977081
Cl[CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[O:12]([CH2:19][CH:20]1[O:25][CH2:24][CH2:23][NH:22][CH2:21]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[O:12]([CH2:19][CH:20]1[O:25][CH2:24][CH2:23][N:22]([CH2:2][C:3]2[NH:4][C:5]3[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=3[N:7]=2)[CH2:21]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 785712-ChloromethylbenzimidazoleHCID 220117952-(Phenoxymethyl)morpholine

Produkt 1

HCID 199644202-((2(RS)-(Phenoxymethyl)morpholin-4-yl)methyl)benzimidazoleAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-(Chloromethyl)benzimidazole (172 mg, 1.03 mmol) and 2(RS)-(phenoxymethyl)morpholine (200 mg) were heated in ethanol (8 ml) at 80° C. (oil bath temperature) in the presence of potassium carbonate (142 mg, 1.03 mmol) for 2 hours. The mixture was cooled then evaporated to dryness. The residue was partitioned between water (10 ml) and ethyl acetate (25 ml). The organic layer was separated and the aqueous re-extracted with ethyl acetate (25 ml). The combined organics were dried (sodium sulphate) then evaporated to give a beige gum which was purified by column chromatography on silica (150 g) using ethyl acetate to ethyl acetate/methanol (25:1) to afford the title compound as a pale yellow solid (220 mg, 66%). mp 171°-172° C. (ethyl acetate/n-hexane). MS, CI+, mz=324 for (M+H)+. 1H NMR (360 MHz, CDCl3) δ2.40 (1H, dd, J1 =J2 =10 Hz), 2.51 (1H, ddd, J1 =3, J2 =J3 =10 Hz), 2.79 (1H, d, J=10 Hz), 2.99 (1H, d, J=10 Hz), 3.82 (1H, ddd, J1 =3, J2 =J3 =10 Hz), 3.91-4.06 (6H, m), 6.88 (2H, dd, J1 =1, J2 =8 Hz), 6.95 (1H, ddd, J1 =1, J2 =J3 =8 Hz), 7.24-7.29 (4H, m), 7.57-7.61 (2H, m). Found: C, 70.55; H, 6.51; N, 12.96. C19H21N3O2 requires C, 70.57; H, 6.55; N, 12.99%.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. customthen evaporated to dryness
  3. customThe residue was partitioned between water (10 ml) and ethyl acetate (25 ml)
  4. customThe organic layer was separated
  5. extractionthe aqueous re-extracted with ethyl acetate (25 ml)
  6. dry with materialThe combined organics were dried (sodium sulphate)
  7. customthen evaporated
  8. customto give a beige gum which
  9. customwas purified by column chromatography on silica (150 g)

Quellen und Nachweise

ORD-Eintrag
ord-a30d1054474d49b8973720ff13c3174a
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614518

Notizen zur Reaktion

Wird geladen…