Triethylamine → HCID 15614722, compound

HRID 845777Notes

Reaction equation

HRID 845777 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C.[NH:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[NH:34][CH:35]1[CH2:40][CH2:39][N:38]([CH2:41][C:42]#[N:43])[CH2:37][CH2:36]1>ClCCl>[O:1]1[CH:5]=[CH:4][C:3]([C:6]([N:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[N:27]=[C:26]2[NH:34][CH:35]2[CH2:36][CH2:37][N:38]([CH2:41][C:42]#[N:43])[CH2:39][CH2:40]2)=[O:8])=[CH:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 102683-Furoic acidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 13588033HCID 13588033, compound

Product 1

HCID 15614722HCID 15614722, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 3.14 parts of 3-furancarboxylic acid, 6 parts of N,N-diethylethanamine and 390 parts of dichloromethane were added 7.2 parts of 2-chloro-1-methylpyridinium iodide. After stirring for 10 minutes at room temperature, 7 parts of 4-[(1H-benzimidazol-2-yl)amino]-1-piperidineacetonitrile were added and the whole was stirred for 1 hour at room temperature. The reaction mixture was washed with water. The organic phase was dried, filtered and evaporated. The residue was crystallized from acetonitrile, yielding 7 parts (74%) of 4-[[1-(3-furanylcarbonyl)-1H-benzimidazol-2-yl]amino]-1-piperidineacetonitrile (intermediate 101).

Workup

  1. stirringthe whole was stirred for 1 hour at room temperature
  2. washThe reaction mixture was washed with water
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-39cd50bd81b8462b8819c534a1620bfe
Source dataset
uspto-grants-1988_07
Patent number
US04760074

Reaction notes

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