Dimethylformamide → HCID 15718907, compound

HRID 2166138Notes

Reaction equation

HRID 2166138 reaction equation
Cl[CH2:2][C:3]#[N:4].[CH2:5]([O:7][CH2:8][CH2:9][N:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[N:12]=[C:11]1[CH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[CH3:6].C(N(CC)CC)C.CN(C)C=O>O>[CH2:5]([O:7][CH2:8][CH2:9][N:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[N:12]=[C:11]1[CH2:19][CH:20]1[CH2:21][CH2:22][N:23]([CH2:2][C:3]#[N:4])[CH2:24][CH2:25]1)[CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 15718837HCID 15718837, compound

Product 1

HCID 15718907HCID 15718907, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.53 parts of chloroacetonitrile, 17.3 parts of 3-(2-ethoxyethyl)-2-(4-piperidinylmethyl)-3H-imidazo[4,5-b]pyridine, 6 parts of N,N-diethylethanamine and 94 parts of N,N-dimethylformamide was stirred for 3 hours at room temperature. The reaction mixture was poured into water and the product was extracted with 1,1'-oxybisethane. The extract was dried, filtered and evaporated, yielding 23.75 parts (100%) of 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidineacetonitrile as a residue (compound 104).

Workup

  1. extractionthe product was extracted with 1,1'-oxybisethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-9c62f61edcfa4c81bb3e5c327d96f8ab
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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