Benzene, (chloromethyl)phenoxy- → (E)-1-[[(2-phenoxyphenyl)methoxy]ethyl]-4-(3-phenyl-2-propenyl)piperazine dihydrochloride

HRID 728798노트

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HRID 728798 반응식
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][Cl:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1(/[CH:22]=[CH:23]/[CH2:24][N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][OH:33])[CH2:27][CH2:26]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(OC(C)(C)C)(C)(C)C.[K]>C(COC)OC>[ClH:11].[ClH:11].[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][O:33][CH2:32][CH2:31][N:28]1[CH2:29][CH2:30][N:25]([CH2:24]/[CH:23]=[CH:22]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:26][CH2:27]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 169302Benzene, (chloromethyl)phenoxy-HCID 782659(E)-4-(3-phenyl-2-propenyl)-1-piperazineethanolHCID 86607002Potassium tert-butyloxide

생성물 1

HCID 67898433(E)-1-[[(2-phenoxyphenyl)methoxy]ethyl]-4-(3-phenyl-2-propenyl)piperazine dihydrochloride

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

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온도
40 °C

실험 절차

7.82 g (3.58 mmol) of o-phenoxybenzyl chloride dissolved in 8 ml of dimethoxyethane were added dropwise at room temperature to a solution of 8.82 g (35.8 mmol) of (E)-4-(3-phenyl-2-propenyl)-1-piperazineethanol and 4.42 g (39.4 mmol) of potassium tert-butyloxide and 4 g of 3A molecular sieve in 125 ml of dry dimethoxyethane. After stirring for 3 days at 40° C., the mixture was cooled to room temperature. The salts in the solution were filtered off and the solution was evaporated. The residue obtained was purified by means of column chromatography over silica (eluent toluene:ethanol=9:1). The collected fractions were dissolved in ethanol and 5 ml of 4.9 N HCl in ethanol was added. The clearsolution was evaporated. Yield 2.4 g (13%), m.p. 221° C.

후처리

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationThe salts in the solution were filtered off
  3. customthe solution was evaporated
  4. customThe residue obtained
  5. customwas purified by means of column chromatography over silica (eluent toluene:ethanol=9:1)
  6. dissolutionThe collected fractions were dissolved in ethanol
  7. addition5 ml of 4.9 N HCl in ethanol was added
  8. customThe clearsolution was evaporated

출처 및 근거

ORD 기록
ord-861e18a1faba469dbd6884b7c8c75614
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05051424

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