Potassium Iodide → 4-[3-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]-3-methoxybenzoic acid methyl ester

HRID 1460224

반응식

HRID 1460224 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.[CH3:23][O:24][C:25](=[O:39])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35]Cl)=[C:28]([O:37][CH3:38])[CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[CH3:23][O:24][C:25](=[O:39])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][N:13]2[CH2:12][CH2:11][CH:10]([C:8]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[OH:9])[CH2:15][CH2:14]2)=[C:28]([O:37][CH3:38])[CH:27]=1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 14407173Methyl 4-(3-chloropropoxy)-3-methoxybenzoate

생성물 1

HCID 144071294-[3-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]-3-methoxybenzoic acid methyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of α,α-bis(4-fluorophenyl)-4-piperidinemethanol (6.0 g, 0.02 mole), 4-(3-chloropropoxy)-3-methoxybenzoic acid methyl ester (5.4 g, 0.021 mole), anhydrous sodium carbonate (7.4 g, 0.07 mole), and potassium iodide (0.3 g) in 150 ml of dimethylformamide was heated on a steam bath for about 20 hr. The mixture was concentrated under reduced pressure, and the residue was partitioned between water and organic solvent (benzene). The organic layer was washed with water and brine and dried over sodium sulfate and eventually crystallized from 2-propanol to give the title compound as a white solid, mp 131°-132.5° C. (2-propanol).

후처리

  1. temperaturewas heated on a steam bath for about 20 hr
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between water and organic solvent (benzene)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customeventually crystallized from 2-propanol

출처 및 근거

ORD 기록
ord-d8c712e2c274493f9acf7df88534363b
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05070087

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