Potassium Iodide → HCID 21428857, compound

HRID 437673Notes

Reaction equation

HRID 437673 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=[O:6].[NH:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[NH:20][C:19]2=[O:27])[CH2:14][CH2:13]1.[I-].[K+]>CN(C)C=O>[O:27]=[C:19]1[N:18]([CH:15]2[CH2:14][CH2:13][N:12]([CH2:2][CH2:3][NH:4][C:5]([C:7]3[O:8][CH:9]=[CH:10][CH:11]=3)=[O:6])[CH2:17][CH2:16]2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[NH:20]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 182358N-(2-Chloroethyl)-2-furamide

Product 1

HCID 21428857HCID 21428857, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.9 parts of N-(2-chloroethyl)-2-furancarboxamide, 9.8 parts of 1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 6.6 parts of potassium iodide and 135 parts of N,N-dimethylformamide is stirred first for 3 hours at reflux and further overnight at room temperature. The reaction mixture is evaporated. The residue is taken up in water and the whole is alkalized. The product is extracted with 4-methyl-2-pentanone. The layers are separated and the aqueous phase is set aside. The organic phase is washed with water, dried, filtered and evaporated. The solid residue is crystallized from 2-propanone. The product is filtered off and dried, yielding a first fraction of 1 part of N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-2-furancarboxamide; mp. 228.9° C. The aqueous phase, which was set aside (see above), is allowed to stand overnight. The precipitated product is filtered off and crystallized from methanol, yielding a second fraction of 4 parts of N-{2-[ 4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-2-furancarboxamide; mp. 231.7° C.

Workup

  1. customThe reaction mixture is evaporated
  2. extractionThe product is extracted with 4-methyl-2-pentanone
  3. customThe layers are separated
  4. washThe organic phase is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue is crystallized from 2-propanone
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-9c1644d304734ff7b8ad182dd94ff22d
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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