1-Methylpiperazine → HCID 3086153, compound

HRID 1902217Notes

Reaction equation

HRID 1902217 reaction equation
Cl[C:2]1[C:3]2[C:4](=[CH:15][S:16][CH:17]=2)[C:5](=[CH:12][C:13]#[N:14])[C:6]2[C:7](=[CH:9][S:10][CH:11]=2)[N:8]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[C:13]([CH:12]=[C:5]1[C:4]2=[CH:15][S:16][CH:17]=[C:3]2[C:2]([N:22]2[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]2)=[N:8][C:7]2=[CH:9][S:10][CH:11]=[C:6]12)#[N:14]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 53924313HCID 53924313, compound

Product 1

HCID 3086153HCID 3086153, compoundYield 85%

Conditions

Temperature
110 °C

Procedure

50 ml of N-methyl-piperazine are added to 14.4 g (52 mmoles) of 5-chloro-9-cyanomethylene-dithieno[3,4-b:4',3'-e]azepine and the mixture is stirred under nitrogen at 110° C. for 2 to 3 hours. After having been cooled, the dark homogeneous reaction mixture is poured onto ice-water and the yellowish crude 9-cyanomethylene-5-(4-methyl-piperazin-1-yl)-dithieno[3,4-b:4',3'-e]azepine is filtered off with suction. After the crude product has been dried in an oven under reduced pressure, it is recrystallized from ethanol, with the addition of active charcoal, or purified by column chromatography (silica gel, mobile phase: a 95/5 mixture of methylene chloride and methanol). 13.6 g (85%) of yellowish 9-cyanomethylene-5-(4-methyl-piperazin-1-yl)-dithieno[3,4-b:4',3'-e]azepine are obtained in the form of a cis/trans-isomer mixture of melting point 148°-151° C.

Workup

  1. temperatureAfter having been cooled
  2. additionthe dark homogeneous reaction mixture is poured onto ice-water
  3. filtrationthe yellowish crude 9-cyanomethylene-5-(4-methyl-piperazin-1-yl)-dithieno[3,4-b:4',3'-e]azepine is filtered off with suction
  4. dry with materialAfter the crude product has been dried in an oven under reduced pressure, it
  5. customis recrystallized from ethanol, with the addition of active charcoal
  6. custompurified by column chromatography (silica gel, mobile phase
  7. additiona 95/5 mixture of methylene chloride and methanol)

Sources & evidence

ORD record
ord-02f8c0fb296a4168879586535bc65b54
Source dataset
uspto-grants-1982_12
Patent number
US04362727

Reaction notes

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