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

HRID 977081노트

반응식

HRID 977081 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-a30d1054474d49b8973720ff13c3174a
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614518

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