Sodium Iodide → 1-[3-(Diphenylamino)propyl]-4-(3-fluorophenyl)-4-piperidinol ethanedioate

HRID 1902671노트

반응식

HRID 1902671 반응식
[C:1]1([N:7]([CH2:14][CH2:15][CH2:16]Br)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:20]=[C:21]([C:25]2([OH:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1.[C:32](=[O:35])([O-:34])[O-].[Na+].[Na+].[I-].[Na+].C(C(C)=[O:43])C>>[C:25]([OH:31])(=[O:43])[C:32]([OH:34])=[O:35].[C:1]1([N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH2:15][CH2:16][N:28]2[CH2:27][CH2:26][C:25]([C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([F:18])[CH:20]=3)([OH:31])[CH2:30][CH2:29]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 5

HCID 5238Sodium IodideHCID 6569Methyl Ethyl KetoneHCID 10340Sodium CarbonateHCID 108273293-[N,N-diphenylamino)-1-bromopropaneHCID 127639064-(3-Fluorophenyl)piperidin-4-ol

생성물 1

HCID 867380231-[3-(Diphenylamino)propyl]-4-(3-fluorophenyl)-4-piperidinol ethanedioate

실험 절차

A mixture of 10.4 g. (0.018 moles) of 3-[N,N-diphenylamino]-1-bromopropane, 3.5 g. (0.018 moles) of 4-(3-fluorophenyl)-4-piperidinol, 1.9 g. (0.018 moles) of sodium carbonate and 1.0 g. of sodium iodide in 100 ml. of methyl ethyl ketone is refluxed for about 3 hours. The reaction is allowed to cool, filtered and the filtrate is evaporated. The residue is shaken with a mixture of diethyl ether and dilute hydrochloric acid. An oily third phase forms which crystallizes on scratching. This material is recrystallized from isopropanol and then from ethanol, and converted back to the free base. The product is then crystallized from isopropanol containing an excess of oxalic acid giving 2.2 g. of 1-[3-(diphenylamino)propyl]-4-(3-fluorophenyl)-4-piperidinol ethanedioate (1:1), mp. 181°-182.5° C.

후처리

  1. additionA mixture of 10.4 g
  2. temperatureto cool
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. customAn oily third phase forms which crystallizes
  6. customThis material is recrystallized from isopropanol
  7. customThe product is then crystallized from isopropanol containing an excess of oxalic acid giving 2.2 g

출처 및 근거

ORD 기록
ord-5242efcf837f40d1816fd3231860f0a6
출처 데이터셋
uspto-grants-1982_12
특허 번호
US04364954

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