Potassium Carbonate → 1-(2-Morpholin-4-ylethyl)-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 494179노트

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HRID 494179 반응식
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C=O)C.O>[N:23]1([CH2:22][CH2:21][N:11]2[C:12]3[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=3)[CH2:8][CH2:9][CH2:10]2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 2525137-Nitro-1,2,3,4-tetrahydroquinolineHCID 111491684-(2-iodoethyl)morpholine

생성물 1

HCID 588741181-(2-Morpholin-4-ylethyl)-7-nitro-1,2,3,4-tetrahydroquinoline수율 7.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
70 °C

실험 절차

To a solution of 7-nitro-1,2,3,4-tetrahydroquinoline (D1) (246 mg, 1.38 mmol) in DMF (2.7 ml) was added potassium carbonate (574 mg, 4.15 mmol) followed by a solution of 4-(2-iodoethyl)morpholine (500 mg, 2.07 mmol) in DMF (2 ml) and the reaction heated to 70° C. After cooling to ambient temperature the reaction mixture was diluted with water and extracted with EtOAc which was washed with water, dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by silica SPE chromatography. Elution with 80% EtOAc/petroleum ether gave the title compound as an orange gum (29 mg). 1H NMR (250 MHz, CDCl3) δ (ppm): 7.39 (m, 2H), 7.00 (d, 1H), 3.73 (m, 4H), 3.47 (m, 2H), 3.38 (m, 2H), 2.79 (t, 2H), 2.49-2.59 (m, 6H), 1.96 (m, 2H).

후처리

  1. temperatureAfter cooling to ambient temperature the reaction mixture
  2. extractionextracted with EtOAc which
  3. washwas washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product which
  7. customwas purified by silica SPE chromatography
  8. washElution with 80% EtOAc/petroleum ether

출처 및 근거

ORD 기록
ord-c1f11253054c41899e4cbefe6415ca3c
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538121B2

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