تفاعل #305229

ord-d8b4da76ffd6425792f0abcc48145e63

معادلة التفاعل

O
water
CC(C)C(=O)Nc1cccc(C2CCN(CCCCS(=O)(=O)[O-])CC2)c1
3-[4-(3-isobutyrylaminophenyl)piperidin-1-yl]propylmethanesulfonate
O=C([O-])[O-].[K+].[K+]
K2CO3
Cc1nc2ccccc2[nH]1
2-methyl-1H-benzimidazole
Cc1nc2ccccc2n1CCCN1CCC(c2cccc(NC(=O)C(C)C)c2)CC1
title compound
المردود 51.0%
Cc1nc2ccccc2n1CCCN1CCC(c2cccc(NC(=O)C(C)C)c2)CC1
2-methyl-1-{3-[4-(3-isobutyrylaminophenyl)piperidin-1-yl]propyl}-1H-benzimidazole
المردود 51.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONby treating the mixture at 80° C. for 5 hours
  2. 2
    استخلاصextracted with ethylacetate (50 ml×2)
  3. 3
    غسيلbeing washed with water
  4. 4
    تجفيفa sodium hydroxide solution, and then the combined organic layer was dried over anhydrous sodium sulfate
  5. 5
    ترشيحfiltered
  6. 6
    أخرىThe solvent was removed from the filtrate under a reduced pressure

الإجراء التجريبي

100 mg (0.75 mmol) of 2-methyl-1H-benzimidazole was dissolved in 5 ml of N,N-dimethylformamide, and 286 mg (0.75 mmol) of 3-[4-(3-isobutyrylaminophenyl)piperidin-1-yl]propylmethanesulfonate and 310 mg (2.25 mmol) of K2CO3 were added to the resulting solution, followed by treating the mixture at 80° C. for 5 hours. The reaction mixture was combined with 50 ml of water and extracted with ethylacetate (50 ml×2) being washed with water and a sodium hydroxide solution, and then the combined organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was removed from the filtrate under a reduced pressure, and the resulting residue was refined by silica gel column chromatography (5% MeOH/CH2Cl2) to obtain 159 mg (yield 51%) of the title compound.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08198307B2uspto-grants-2012_06