Sodium Iodide → HCID 18946279, compound

HRID 1768961Notes

Reaction equation

HRID 1768961 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11]Cl)[CH2:5][CH2:4]1)=[O:2].[NH2:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][C:19]#[N:20])=[CH:16][CH:15]=1.[I-].[Na+].[OH-].[Na+]>O>[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][NH:13][C:14]2[CH:22]=[CH:21][C:17]([CH2:18][C:19]#[N:20])=[CH:16][CH:15]=2)[CH2:5][CH2:4]1)=[O:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 770004-AminophenylacetonitrileHCID 6422658HCID 6422658, compound

Product 1

HCID 18946279HCID 18946279, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-formyl-4-(3-chloropropyl)piperazine (1.0 g, 5.2 mmol) prepared according to step a) above, 4-aminobenzylcyanide (0.66 g, 5 mmol) and sodium iodide (0.15 g, 1 mmol) was heated at 100°-105° C. for 2 hours. After cooling the mixture was dissolved in 40 ml of water and treated with decolorizing carbon. The filtered solution was made alkaline with 2N aqueous NaOH and extracted with chloroform (3×20 ml). The organic extracts were washed with water, dried over MgSO4 and concentrated. The residue was chromatographed on a silica gel column eluting with a 2:1 mixture of ethyl acetate and methanol to give the title compound. Yield: 0.55 g, 38.5%. Mp. after trituration with ether: 85°-87° C.

Workup

  1. customprepared
  2. temperaturewas heated at 100°-105° C. for 2 hours
  3. temperatureAfter cooling the mixture
  4. additiontreated with decolorizing carbon
  5. extractionextracted with chloroform (3×20 ml)
  6. washThe organic extracts were washed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was chromatographed on a silica gel column
  10. washeluting with a 2:1 mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-bb13bccca09448c0bea14694ad587afe
Source dataset
uspto-grants-1995_01
Patent number
US05380724

Reaction notes

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