Dichloromethane → HCID 178480253, compound

HRID 1460502Notes

Reaction equation

HRID 1460502 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH3:10][N:11]1[CH2:19][CH2:18][CH2:17][CH:13]([C:14](O)=O)[CH2:12]1.[OH-].[Na+].C(Cl)Cl>O>[CH3:10][N:11]1[CH2:19][CH2:18][CH2:17][CH:13]([C:14]2[NH:1][C:2]3=[N:3][CH:4]=[CH:5][CH:6]=[C:7]3[N:8]=2)[CH2:12]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 99562,3-DiaminopyridineHCID 14798Sodium HydroxideHCID 125147111-Methylpiperidine-3-carboxylic acid hydrochloride

Product 1

HCID 178480253HCID 178480253, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Grams 10.9 of 2,3-diaminopyridine and 17,9 g N-methylnipecotic acid hydrochloride are heated at 190° C. for 6 hours. The reaction mixture is cooled and diluted with a small amount of water, then is made alkaline to pH 10 by addition of NaOH and extraction is repeated several times with methylene chloride. The organic extracts, collected together, are evaporated to dryness. The obtained residue, is extracted several times with diethyl ether and the ethereal extracts are evaporated to dryness. The obtained residue, crystallized from acetonitrile, provides 5 g (23% of the theoretical value) 2-(1-methylpiperidin-3-yl)-3H-imidazo-[4,5-b] pyridine melting at 141°-144° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe organic extracts, collected together
  3. customare evaporated to dryness
  4. extractionThe obtained residue, is extracted several times with diethyl ether
  5. customthe ethereal extracts are evaporated to dryness
  6. customThe obtained residue, crystallized from acetonitrile

Sources & evidence

ORD record
ord-a3cf8bb32ef941abb73694918d4634d7
Source dataset
uspto-grants-1991_12
Patent number
US05071855

Reaction notes

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