1-Butanol → 4-[Bis(4-fluorophenyl)methyl]-1-[3-(3,4-dimethoxyphenoxy)propyl]piperidine oxalate

HRID 1709880노트

반응식

HRID 1709880 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1.[C:37](=[O:40])([O-:39])[O-].[K+].[K+].[I-].[K+].C([OH:49])CCC>>[C:36]([OH:35])(=[O:49])[C:37]([OH:39])=[O:40].[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=3)[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

참가 물질

6

반응물 5

HCID 2631-ButanolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132105144-(3-Chloropropoxy)-1,2-dimethoxybenzeneHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidine

생성물 1

HCID 230363874-[Bis(4-fluorophenyl)methyl]-1-[3-(3,4-dimethoxyphenoxy)propyl]piperidine oxalate

실험 절차

A mixture of 6.02 g (0.021 mole) of 4-[bis(4-fluorophenyl)-methyl]piperidine, 4.83 g (0.021 mole) of 4-(3-chloropropoxy)-1,2-dimethoxybenzene, and potassium carbonate (5.52 g, 0.04 mole) was heated at reflux overnight in 300 ml of 1-butanol containing potassium iodide (0.3 g). The reaction mixture was concentrated to dryness and partitioned between chloroform and water several times. The chloroform layer was dried over anhydrous sodium sulfate and then filtered. The chloroform was removed by rotary evaporator. The oil obtained was converted to the oxalate salt and then recrystallized from ethanol-ethyl ether and methanol isopropyl ether. This furnished 7.77 g (64.7%) of white solid, m.p. 188° C.

후처리

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrated to dryness
  3. custompartitioned between chloroform and water several times
  4. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe chloroform was removed by rotary evaporator
  7. customThe oil obtained
  8. customrecrystallized from ethanol-ethyl ether and methanol isopropyl ether

출처 및 근거

ORD 기록
ord-7eba9704c1124bc0b280658b0d339c28
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04950674

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