HCID 13187608, compound → HCID 13187611, compound

HRID 1388114Notes

Reaction equation

HRID 1388114 reaction equation
[ClH:1].Cl.[C:3]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([NH:21][CH2:22][C:23]#[N:24])[CH2:17][CH2:16]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:25]([O-])=[O:26].[Na+]>O>[ClH:1].[ClH:1].[C:3]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([N+:21]2[N-:25][O:26][C:23](=[NH:24])[CH:22]=2)[CH2:17][CH2:16]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 13187608HCID 13187608, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13187611HCID 13187611, compoundYield 137.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

5.0 g of 4-(4-benzoylbutyl)-1-(cyanomethylamino)piperazine dihydrochloride was dissolved in 50 ml of water, and under ice cooling, a solution of 2.0 g of sodium nitrite in 20 ml of water was added dropwise. The reaction was carried out for 1 hour. The reaction mixture was extracted with chloroform. Chloroform was evaporated, and the residue was dissolved in 30 ml of methanol. Then, 30 ml of 12% ethanolic hydrochloric acid was added, and the reaction was carried out for two days at room temperature. The precipitated crystals were collected by filtration to give 3.7 g of the title compound having a melting point of 168° C. (decomp.).

Workup

  1. extractionThe reaction mixture was extracted with chloroform
  2. customChloroform was evaporated
  3. dissolutionthe residue was dissolved in 30 ml of methanol
  4. additionThen, 30 ml of 12% ethanolic hydrochloric acid was added
  5. waitthe reaction was carried out for two days at room temperature
  6. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-66079677ab8840e8aeb885db5280e6bf
Source dataset
uspto-grants-1984_02
Patent number
US04430342

Reaction notes

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