4-Chlorophenylacetyl chloride → 2-amino-7-(p-chlorophenylacetyl)-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine

HRID 647482Notes

Reaction equation

HRID 647482 reaction equation
Br.Br.[NH2:3][C:4]1[CH:5]=[N:6][C:7]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9][C:8]=2[N:14]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](Cl)=[O:24])=[CH:18][CH:17]=1>[OH-].[Na+].O1CCOCC1>[NH2:3][C:4]1[CH:5]=[N:6][C:7]2[CH2:13][CH2:12][N:11]([C:23](=[O:24])[CH2:22][C:19]3[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=3)[CH2:10][CH2:9][C:8]=2[N:14]=1

Participants

5

Reactant 2

HCID 906924-Chlorophenylacetyl chlorideHCID 204363772-amino-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine dihydrobromide

Product 1

HCID 204364612-amino-7-(p-chlorophenylacetyl)-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

5.8 gm (17.9 mmols) of 2-amino-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine dihydrobromide were dissolved in 50 ml of 2 N sodium hydroxide, and the solution was admixed dropwise with an ice-cooled solution of 7.5 gm of p-chlorophenyl-acetyl chloride in 50 ml of dioxane. The resulting mixture was stirred overnight and then evaporated, and the residue was extracted with chloroform. The chloroform extract was dried and then evaporated, and the residue was triturated with carbon tetrachloride and suction-filtered.

Workup

  1. customevaporated
  2. extractionthe residue was extracted with chloroform
  3. extractionThe chloroform extract
  4. customwas dried
  5. customevaporated
  6. customthe residue was triturated with carbon tetrachloride
  7. filtrationsuction-filtered

Sources & evidence

ORD record
ord-b600ed6958ab47a9aa77d5440918b0d7
Source dataset
uspto-grants-1983_10
Patent number
US04409220

Reaction notes

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