Trimethylamine → 1,2,3,9-Tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one

HRID 36773

反応式

HRID 36773 の反応式
CC1N([CH2:7][CH:8]2[C:21](=[O:22])[C:12]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[N:19]([CH3:20])[C:11]=3[CH2:10][CH2:9]2)C=CN=1.CI.CN(C)C>>[CH3:20][N:19]1[C:11]2[CH2:10][CH2:9][C:8](=[CH2:7])[C:21](=[O:22])[C:12]=2[C:13]2[C:18]1=[CH:17][CH:16]=[CH:15][CH:14]=2

参加物

4

反応物 3

HCID 1146TrimethylamineHCID 4595OndansetronHCID 6328Methyl iodide

生成物 1

HCID 117905051,2,3,9-Tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one

実験手順

Peculiarly, the above-said patent specification indicates this tertiary amine to be known per se and, in addition, ondansetron can be prepared therefrom in an other way, too. After quaternizing the tertiary amine with methyl iodide, trimethylamine is split off from the obtained methoiodide by Hofmann's elimination reaction to give 9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one. The thus-obtained electrophilic conjugated enone is subjected to an addition reaction with 2-methylimidazole (see Example 8 of the specification). The surprisingly moderate yield of 43.2% of the reaction shows that the significance of this simple direct addition, starting from the separated enone, should not be overestimated.

後処理

  1. customcan be prepared
  2. customis split off from the obtained methoiodide by Hofmann's elimination reaction

出典と根拠

ORDレコード
ord-c36be793b02543d6ad007afe1cf74764
出典データセット
uspto-grants-1995_05
特許番号
US05416221

関連ノート

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