تفاعل #162289

ord-30575c2547764b6dbeda56b31010f9e9

معادلة التفاعل

O=S(=O)(Cl)c1ccc(Cl)cc1
4-chlorobenzenesulphonyl chloride
CC(C)(C)OC(=O)N1CCC(CN)CC1
tert-butyl 4-(aminomethyl)piperidine-1-carboxylate
CCN(C(C)C)C(C)C
diisopropylethylamine
CC(C)(C)OC(=O)N1CCC(CNS(=O)(=O)c2ccc(Cl)cc2)CC1
product
المردود 88.0%
CC(C)(C)OC(=O)N1CCC(CNS(=O)(=O)c2ccc(Cl)cc2)CC1
tert-Butyl 4-[(4-chlorobenzenesulphonylamino)methyl]piperidine-1-carboxylate
المردود 88.0%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    غسيلThe organic phase is washed with 10 ml of water
  2. 2
    تجفيفIt is dried over sodium sulphate
  3. 3
    أخرىevaporated to dryness in order

الإجراء التجريبي

A solution of 0.844 g (4 mmol) of 4-chlorobenzenesulphonyl chloride in 5 ml of dichloromethane is added dropwise to a solution of 0.857 g (4 mmol) of tert-butyl 4-(aminomethyl)piperidine-1-carboxylate, 0.99 ml (6 mmol) of diisopropylethylamine and 0.024 g (0.2 mmol) of 4-dimethylaminopyridine in 9 ml of dichloromethane. The mixture is stirred at ambient temperature overnight. The organic phase is washed with 10 ml of water and then 4 ml of a 1N aqueous hydrochloric acid solution, 2 times 14 ml of water, 2 times 14 ml of a 1N aqueous sodium hydroxide solution, 3 times 14 ml of water and 14 ml of a saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated to dryness in order to obtain 1.371 g (3.52 mmol) of product in the form of an orange paste used as is in the following stage.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08835418B2uspto-grants-2014_09