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

HRID 647487Notes

Reaction equation

HRID 647487 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 2 N 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-73f2dcac85ab427baa972df7aaeca814
Source dataset
uspto-grants-1983_10
Patent number
US04409220

Reaction notes

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