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

HRID 2045816Notes

Reaction equation

HRID 2045816 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 the mixture is heated to 145° C. for 5 hours. Excess piperazine is distilled off and the residue is treated with dichloromethane and methanol. Any product precipitated 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. customAny product precipitated
  4. filtrationfiltered
  5. custompurified by chromatography (Alox, dioxane/toluene/methanol/NH4OH 50/20/20/2)

Sources & evidence

ORD record
ord-a987bff9d5e3414c885614ff03dc2139
Source dataset
uspto-grants-2013_11
Patent number
US08592400B2

Reaction notes

Loading…