تفاعل #1869160

ord-e2ceadb7003543839098c55a9adcf662

معادلة التفاعل

CN1CCC(=O)CC1
1-methyl-4-piperidone
C[O-].[Na+]
sodium methoxide
O=S(=O)(Nc1ccc2[nH]ccc2c1)c1cccc2ccccc12
N-[1H-indol-5-yl]naphthalene-1-sulphonamide
CN1CC=C(c2c[nH]c3ccc(NS(=O)(=O)c4cccc5ccccc45)cc23)CC1
N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide
المردود 52.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةthe resulting solution is heated
  2. 2
    درجة الحرارةto reflux for 48 hours
  3. 3
    تركيزThe reaction mixture is concentrated at reduced pressure
  4. 4
    أخرىthe residue obtained
  5. 5
    أخرىis purified by chromatography over silica gel

الإجراء التجريبي

To a solution of 712 mg (13.2 mMol) of sodium methoxide in 100 ml of methanol are added 850 mg (2.64 mMol) of N-[1H-indol-5-yl]naphthalene-1-sulphonamide followed by 596 mg (5.28 mMol) of 1-methyl-4-piperidone and the resulting solution is heated to reflux for 48 hours. The reaction mixture is concentrated at reduced pressure and the residue obtained is purified by chromatography over silica gel, using as eluent mixtures of methylene chloride/methanol/ammonia, to yield 573 mg (52%) of N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide as a solid with m.p.=244-245° C.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07498328B2uspto-grants-2009_03