1-Chloro-2-fluorobenzene → 6-Chloro-1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] maleate

HRID 1632856ノート

反応式

HRID 1632856 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.[H-].[Na+].[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1F.[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31]>CS(C)=O.CCOCC>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[Cl:19])[CH2:9][C:10]3([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 95831-Chloro-2-fluorobenzeneHCID 24758Sodium hydrideHCID 444266Maleic AcidHCID 128016176-Chloro-1'-methylspiro[indoline-3,4'-piperidine]

生成物 1

HCID 128016266-Chloro-1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] maleate

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
45 °C

実験手順

A mixture of 2.4 g of 6-chloro-1'-methylspiro[indoline-3,4'-piperidine], Example 23b, 0.5 g of sodium hydride (99%) and 6 g of 2-chlorofluorobenzene in 25 ml of dimethylsulfoxide is stirred at 45° C. under nitrogen for 1 hour. Thereafter, the mixture is quenched with ice-water before being extracted thrice with ether. The combined ether extracts are successively washed with water, dried and concentrated under vacuum leaving a reddish oil. The oil is passed through an alumina column, ether eluant, and the purified oil, in ether, is converted to its maleic acid salt. The salt is recrystallized from an acetone-ether mixture to provide off-white platelets, mp 172°-173° C. of 6-chloro-1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] maleate.

後処理

  1. customThereafter, the mixture is quenched with ice-water
  2. extractionbefore being extracted thrice with ether
  3. washThe combined ether extracts are successively washed with water
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customleaving a reddish oil
  7. customThe salt is recrystallized from an acetone-ether mixture

出典と根拠

ORDレコード
ord-9f1628305c14498eaf0580b63eca5b69
出典データセット
uspto-grants-1984_10
特許番号
US04477667

反応ノート

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