Potassium Carbonate → 9-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-1,2,3,4-tetrahydro-acridine

HRID 2251101노트

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HRID 2251101 반응식
[CH2:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1.Cl[CH2:23][CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[N:26]1([CH2:25][CH2:24][CH2:23][O:21][C:18]2[CH:19]=[CH:20][C:15]([C:13]3[C:12]4[C:7]([N:6]=[C:5]5[C:14]=3[CH2:1][CH2:2][CH2:3][CH2:4]5)=[CH:8][CH:9]=[CH:10][CH:11]=4)=[CH:16][CH:17]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 113210281-(3-Chloropropyl)-pyrrolidineHCID 1360572454-(1,2,3,4-Tetrahydro-acridin-9-yl)-phenol

생성물 1

HCID 115672189-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-1,2,3,4-tetrahydro-acridine

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
80 °C

실험 절차

The product from the previous step, 4-(1,2,3,4-Tetrahydro-acridin-9-yl)-phenol (22 mg, 0.08 mmol), 1-(3-Chloropropyl)-pyrrolidine (18 mg, 0.12 mmol), and K2CO3 (17 mg, 0.12 mmol) were mixed in NMP (267 uL) and stirred rapidly at 80° C. for 90 minutes in a sealed vial. The reaction mixture was cooled, partitioned between Et2O (50 mL) and H2O (10 mL). The organic layer was washed with H2O (3×10 mL), sat. aq. NaCl (10 mL), dried over Na2SO4, decanted and concentrated. The residue was purified using preparative LCMS to give product the desired product.

후처리

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between Et2O (50 mL) and H2O (10 mL)
  3. washThe organic layer was washed with H2O (3×10 mL), sat. aq. NaCl (10 mL)
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated
  7. customThe residue was purified

출처 및 근거

ORD 기록
ord-f2a3fe71566e47c0bd2b0e32fcc1ca25
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07319103B2

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