The Reaction of Tertiary Amines with Arenesulfonyl Chloridest

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Other Title
  • 芳香族スルホン酸クロリドと第三級アミンの反応
  • 親電子試薬と第三級アミンの反応　Ｉ　　芳香族スルホン酸クロリドと第三級アミンの反応

Description

1-Azabicyclo[2.2.2]octane (ABCO) gave 1-arylsulfonyl-4-(2-chloroethyl) piperidines [2a-e] in good yields by the reactions with arenesulfonyl chlorides [1a-e] in benzene. The effects of reaction solvents (Fig.4), temperatures (Fig.2 and 3, Table 2), and the substituents on the arenesulfonyl chlorides were investigated. In the reactions, 1-[2-(1-arylsulfonyl4-piperidinyl) ethyl]quinuclidinium salts (e. g. [5]) were obtained as a minor product.1, 4Diazabicyclo[2.2.2]octane (DABCO) gave similar products [6a-e] by the reactions with arenesulfonyl chlorides. The reactions of [1a] with some other tertiary amines such as triethylamine, 1-methylpyrrolidine, 1-methyl and 1-ethylpiperidine, and 1-methylmorpholine were also investigated.4-Methylpyrrolidine gave N-(4-chlorobutyl)-N-methyl-p-toluenesulfonamide [7] in a good yield at 60°C in benzene but the other amines gave only a small amount, if any, of sulfonamides under the similar reaction conditions.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1984 (8), 1279-1286, 1984-08-10

    The Chemical Society of Japan

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