Sodium Hydroxide → 2-(2-{4-[1-(3-[1,3]dioxolan-2-yl-propyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoic Acid

HRID 457789

반응식

HRID 457789 반응식
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1.[H-].[Na+].Cl[CH2:32][CH2:33][CH2:34][CH:35]1[O:39][CH2:38][CH2:37][O:36]1.[OH-].[Na+]>CN(C=O)C.C(O)C>[O:36]1[CH2:37][CH2:38][O:39][CH:35]1[CH2:34][CH2:33][CH2:32][N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([CH:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][O:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:28])=[O:2])[CH2:14][CH2:15]2)=[CH:20]1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 5520722-(3-Chloropropyl)-1,3-dioxolaneHCID 11440344methyl 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoate

생성물 1

HCID 102275642-(2-{4-[1-(3-[1,3]dioxolan-2-yl-propyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoic Acid

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매3회

실험 절차

A solution of 2.75 g (7 mmol) of 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoic acid methyl ester (prepared as in Example 1, part D) in 10 mL of anhydrous DMF was added to a suspension of 0.36 g (9.1 mmol) of a NaH (60% dispersion in mineral oil) in 5 mL of anhydrous DMF under an inert atmosphere. After stirring for 30 minutes at room temperature, a solution of 1.1 mL (8.4 mmol) of 2-(3-chloro-propyl)-[1,3]dioxolane in 3 mL of DMF was added. The crude mixture was stirred at room temperature for 16 hours and the solvent was removed under reduced pressure. The residue obtained was dissolved with 150 mL of ethanol and 6 mL of a 2N NaOH aqueous solution were added. After 12 h at room temperature, the solvent was removed under reduced pressure. The crude mixture was dissolved with 50 mL of water and neutralised with a 2N HCl aqueous solution. The crude mixture was purified by flash chromatography over silica gel affording 0.83 g (29% of yield) of the expected product.

후처리

  1. customthe solvent was removed under reduced pressure
  2. customThe residue obtained
  3. additionwere added
  4. waitAfter 12 h at room temperature
  5. customthe solvent was removed under reduced pressure
  6. dissolutionThe crude mixture was dissolved with 50 mL of water and neutralised with a 2N HCl aqueous solution
  7. customThe crude mixture was purified by flash chromatography over silica gel affording 0.83 g (29% of yield) of the expected product

출처 및 근거

ORD 기록
ord-06bb16c5ca144ad3a790b4f00ec27b91
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189741B2

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