Sodium Hydroxide → 2-Amino-3-chloro-7-ethyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine hydrochloride

HRID 1153767Notes

Reaction equation

HRID 1153767 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:11][CH2:10][N:9]([CH2:12][CH3:13])[CH2:8][CH2:7][C:6]=2[N:14]=1.[Cl:15]Cl.[OH-].[Na+]>C(O)(=O)C>[ClH:15].[NH2:1][C:2]1[C:3]([Cl:15])=[N:4][C:5]2[CH2:11][CH2:10][N:9]([CH2:12][CH3:13])[CH2:8][CH2:7][C:6]=2[N:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24526ChlorineHCID 30678372-Amino-7-ethyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine

Product 1

HCID 204363752-Amino-3-chloro-7-ethyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6 gm (31.3 mmols) of 2-amino-7-ethyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine were dissolved in 100 ml of glacial acetic acid and, while cooling the solution with ice, chlorine was introduced until the thin-layer chromatogram showed that no more starting material was present. Thereafter, the reaction mixture was made alkaline with 2N sodium hydroxide and was then extracted with chloroform. The chloroform extract solution was evaporated, and the residue was column-chromatographically purified on silicagel with ethyl acetate/methanol/ethanolic ammonia (4:1:0.5) as the mobile phase. The hydrochloride was precipitated from ethanol with ethanolic hydrochloric acid.

Workup

  1. additionwas introduced until the thin-layer chromatogram
  2. extractionwas then extracted with chloroform
  3. extractionThe chloroform extract solution
  4. customwas evaporated
  5. custompurified on silicagel with ethyl acetate/methanol/ethanolic ammonia (4:1:0.5) as the mobile phase
  6. customThe hydrochloride was precipitated from ethanol with ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-9b0741da2cc849b5a41a35cee172d755
Source dataset
uspto-grants-1984_12
Patent number
US04486433

Reaction notes

Loading…