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

HRID 648355ノート

反応式

HRID 648355 の反応式
[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

参加物

6

反応物 5

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

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-4fd70594539940c88e39080309ecc674
出典データセット
uspto-grants-1983_10
特許番号
US04411904

反応ノート

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