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

HRID 1153762Notes

Reaction equation

HRID 1153762 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-].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 961HydroxideSolventHCID 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 2N 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-85652589ab6c4f1fa946c4b4a69f3106
Source dataset
uspto-grants-1984_12
Patent number
US04486433

Reaction notes

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