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

HRID 2251101ノート

反応式

HRID 2251101 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f2a3fe71566e47c0bd2b0e32fcc1ca25
出典データセット
uspto-grants-2008_01
特許番号
US07319103B2

反応ノート

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