Dimethylformamide → HCID 13588022, compound

HRID 330541Notes

Reaction equation

HRID 330541 reaction equation
Cl[CH2:2][C:3]#[N:4].[CH3:5][C:6]1[O:10][C:9]([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[NH:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[CH3:5][C:6]1[O:10][C:9]([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[NH:21][CH:22]2[CH2:27][CH2:26][N:25]([CH2:2][C:3]#[N:4])[CH2:24][CH2:23]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 10340Sodium CarbonateHCID 14677561HCID 14677561, compound

Product 1

HCID 13588022HCID 13588022, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 2 parts of 2-chloroacetonitrile, 8 parts of 1-[(5-methyl-2-furanyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine, 3.1 parts of sodium carbonate and 90 parts of N,N-dimethylformamide was stirred and heated overnight at 45° C. The reaction mixture was poured into water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane, yielding 7.3 parts (80.4%) of 4-[[1-[(5-methyl-2-furanyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidineacetonitrile; mp. 177.3° C. (int. 36).

Workup

  1. extractionthe product was extracted with dichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-634d12cd12e443f7b7025d36e34d6d27
Source dataset
uspto-grants-1990_01
Patent number
US04897401

Reaction notes

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