3-[4-(4-Chlorophenyl)piperazin-1-yl]propan-1-ol → 4-(3-Trifluoromethylphenyl)-1-[3-(3,4-ethylenedioxyphenylcarbamoyloxy)propyl]piperazine, hydrochloride

HRID 5855

반응식

HRID 5855 반응식
[CH2:1]1[CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([N:11]=[C:12]=[O:13])=[CH:4][C:3]=2[O:2]1.[F:14][C:15]([F:33])([F:32])[C:16]1[CH:17]=[C:18]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH2:30][OH:31])[CH2:24][CH2:23]2)[CH:19]=[CH:20][CH:21]=1.[Cl:34]C1C=CC(N2CCN(CCCO)CC2)=CC=1>C1(C)C=CC=CC=1>[ClH:34].[F:33][C:15]([F:14])([F:32])[C:16]1[CH:17]=[C:18]([N:22]2[CH2:23][CH2:24][N:25]([CH2:28][CH2:29][CH2:30][O:31][C:12](=[O:13])[NH:11][C:5]3[CH:6]=[CH:7][C:8]4[O:9][CH2:10][CH2:1][O:2][C:3]=4[CH:4]=3)[CH2:26][CH2:27]2)[CH:19]=[CH:20][CH:21]=1

참가 물질

5

반응물 3

HCID 2340503-[4-(4-Chlorophenyl)piperazin-1-yl]propan-1-olHCID 27761726-Isocyanato-2,3-dihydro-1,4-benzodioxineHCID 155725143-{4-[3-(Trifluoromethyl)phenyl]piperazin-1-yl}propan-1-ol

생성물 1

HCID 1317181644-(3-Trifluoromethylphenyl)-1-[3-(3,4-ethylenedioxyphenylcarbamoyloxy)propyl]piperazine, hydrochloride수율 68.7%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

A mixture of 3,4-ethylenedioxyphenylisocyanate (2.0 mmol) (produced as in Example 16) and 3-[4-(3-trifluoromethyl-phenyl) -1-piperazinyl]propanol (580 mg; 2.0 mmol) in toluene (30 ml) was refluxed for 16 h. To the crude product was added 3-[4-(4-chlorophenyl)-1-piperazinyl]propanol (510 mg; 2.0 mmol) in toluene (30 ml) and refluxed for 16 h. The solvent was evaporated and the residue resuspended in ethyl acetate, filtered and evaporated to dryness. The residue was submitted to flash chromatography on silica gel 60 eluting with toluene/ethyl acetate (1:1) graduated to toluene/ethyl acetate (1:3). The product was taken up in ethanol, which was treated with hydrogen chloride in ether to give 690 mg of the title compound. M.p. 242°-245° C. MS (70 eV): m/z 465 (34%, M+), 450 (11), 288 (25), 265 (21), 243 (100), 177 (61), 70 (79).

후처리

  1. temperaturewas refluxed for 16 h
  2. temperaturerefluxed for 16 h
  3. customThe solvent was evaporated
  4. filtrationfiltered
  5. customevaporated to dryness
  6. additionwhich was treated with hydrogen chloride in ether

출처 및 근거

ORD 기록
ord-670859b83ec7444589c35a833a5ac749
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246935

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