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Sodium Iodide → 2-{3-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]propyl-amino}-N,N-dimethylbenzamide

HRID 2294148
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HRID 2294148 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.Cl[CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=1[C:23]([N:25]([CH3:27])[CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH2:17][CH2:18][CH2:19][NH:20][C:21]3[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=3[C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH2:12][CH2:13]2)[CH:7]=1
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반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2735754HCID 2735754, 화합물HCID 214734352-(3-chloropropyl)amino-N,N-dimethylbenzamide

생성물 1

HCID 214734652-{3-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]propyl-amino}-N,N-dimethylbenzamide수율 40.6%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6342Acetonitrile용매

실험 절차

A mixture of 1-(5-chloro-2-methoxyphenyl)piperazine (365 mg, 1.6 mmol), prepared as in Example 2, 2-(3-chloropropyl)amino-N,N-dimethylbenzamide (385 mg of crude mixture), prepared as in Example 28, potassium carbonate (550 mg, 3.98 mmol) and sodium iodide (240 mg, 1.6 mmol) in 20 mL of acetonitrile was heated at reflux for 18 hours. The mixture was poured into water and extracted with ethyl acetate (2×50 mL). The combined extract was washed with brine, dried (MgSO4) and concentrated. The residue was purified on silica gel by flash chromatography eluting with 6% methanol/methylene chloride to give 2-{3-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl ]propylamino}-N,N-dimethylbenzamide (280 mg, 0.65 mmol).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel by flash chromatography
  9. washeluting with 6% methanol/methylene chloride

출처 및 근거

ORD 기록
ord-46b0388b059643fb89553b61e5746c23
출처 데이터셋
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05688795

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