Potassium Carbonate → 2-[3-(4-Methoxy-1-piperidinyl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 1669215

반응식

HRID 1669215 반응식
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Br[CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[C:16]3[C:15](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]2=[O:23])[CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 776664-Methoxypiperidine

생성물 1

HCID 574476972-[3-(4-Methoxy-1-piperidinyl)propyl]-1H-isoindole-1,3(2H)-dione수율 59.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

A suspension of 4-methoxypiperidine (286) (4.1 g, 35.3 mmol), N-(3-bromopropyl)phthalimide (9.0 g, 33.6 mmol) and K2CO3 (7.0 g, 50.4 mmol) in DMF (80 mL) was stirred at 50° C. for 16 h. The solution was cooled, the solvent evaporated and the residue partitioned between water (150 mL) and EtOAc (150 mL). The organic fraction was washed with water (2×50 mL) and brine (50 mL), dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-5%) of MeOH/DCM, to give phthalimide 305 (6.0 g, 59%) as a white solid: 1H NMR δ 7.81-7.86 (m, 2H, Harom), 7.67-7.73 (m, 2H, Harom), 3.75-3.79 (t, J=7.0 Hz, 2H, CH2N), 3.28 (s, 3H, OCH3), 3.09-3.17 (m, 1H, CHO), 2.63-2.70 (m, 2H, CH2N), 2.39 (t, J=7.0 Hz, 2H, CH2N), 2.01-2.08 (m, 2H, CH2N), 1.85 (p, J=7.0 Hz, 2H, CH2), 1.74-1.81 (m, 2H, CH2), 1.37-1.46 (m, 2H, CH2). Anal. calcd for C17H22N2O3: C, 67.5; H, 7.3; N, 9.3. Found: C, 67.3; H, 7.4; N, 9.3%.

후처리

  1. temperatureThe solution was cooled
  2. customthe solvent evaporated
  3. customthe residue partitioned between water (150 mL) and EtOAc (150 mL)
  4. washThe organic fraction was washed with water (2×50 mL) and brine (50 mL)
  5. customdried
  6. customthe solvent evaporated
  7. customThe residue was purified by chromatography
  8. washeluting with a gradient (0-5%) of MeOH/DCM

출처 및 근거

ORD 기록
ord-9b7b960dd3fe4fb9a99f863ec5ee8752
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989451B2

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