Piperazine → 7-ethyl-2-piperazin-1-yl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine

HRID 330884Notes

Reaction equation

HRID 330884 reaction equation
Cl[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.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>>[CH2:12]([N:9]1[CH2:10][CH2:11][C:5]2[N:4]=[CH:3][C:2]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[N:14][C:6]=2[CH2:7][CH2:8]1)[CH3:13]

Participants

3

Reactant 2

HCID 4837PiperazineHCID 580715892-chloro-7-ethyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine

Product 1

HCID 580716007-ethyl-2-piperazin-1-yl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepineYield 52.6%

Conditions

Temperature
145 °C

Procedure

3 g 2-chloro-7-ethyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine are combined with 23.3 g piperazine and heated to 145° C. for 5 hours. Excess piperazine is distilled off and the residue is treated with dichloromethane and methanol. Precipitated product is suction filtered and purified by chromatography (Alox, dioxane/toluene/methanol/NH4OH 50/20/20/2). 1.95 g product are obtained.

Workup

  1. distillationExcess piperazine is distilled off
  2. additionthe residue is treated with dichloromethane and methanol
  3. filtrationfiltered
  4. custompurified by chromatography (Alox, dioxane/toluene/methanol/NH4OH 50/20/20/2)

Sources & evidence

ORD record
ord-f6d5196343ae43b681ed94d273b29d1d
Source dataset
uspto-grants-2014_11
Patent number
US08877758B2

Reaction notes

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