Triethylamine → HCID 70382071, compound

HRID 1252670Notes

Reaction equation

HRID 1252670 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[CH:15]=[CH:14][C:13](=[CH:16][C:17]#[N:18])[CH2:12][C:7]32[CH2:11][S:10][CH2:9][C:8]=13.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>CN(C)C=O>[C:17]([CH:16]=[C:13]1[CH2:12][C:7]23[CH2:11][S:10][CH2:9][C:8]2=[C:2]([N:23]2[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]2)[CH:3]=[CH:4][N:5]=[C:6]3[CH:15]=[CH:14]1)#[N:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 70418612HCID 70418612, compound

Product 1

HCID 70382071HCID 70382071, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

11.6 g (43 millimoles) of 4-chloro-10-cyanomethylenethieno[4,3-e]benzoazepine were dissolved in 70 ml of dimethylformamide, and 10 ml (90 millimoles) of N-methylpiperazine and 10 ml (75 millimoles) of triethylamine were added, a highly exothermic reaction taking place. The mixture was stirred for from 2 to 3 hours at 100° C. under nitrogen, the dark homogeneous reaction mixture was then cooled and poured onto ice water, the yellowish crude product 10-cyanomethylene-4-(4-methylpiperazin-1-yl)-thieno[4,3-e]benzoazepine, was filtered off under suction. The crude product was dried in a drying oven under reduced pressure and then recrystallized from ethanol with the addition of active carbon or purified by column chromatography (silica gel, mobile phase 95:5 methylene chloride/methanol). 11.6 g (81%) of yellowish 10-cyanomethylene4-(4-methylpiperazin-1-yl)-thieno[4,3-e]benzoazepine were obtained in the form of a cis/trans isomer mixture of melting point 90°-92° C.

Workup

  1. customa highly exothermic reaction
  2. temperaturethe dark homogeneous reaction mixture was then cooled
  3. additionpoured onto ice water
  4. filtrationthe yellowish crude product 10-cyanomethylene-4-(4-methylpiperazin-1-yl)-thieno[4,3-e]benzoazepine, was filtered off under suction
  5. dry with materialThe crude product was dried in a drying oven under reduced pressure
  6. customrecrystallized from ethanol with the addition of active carbon
  7. custompurified by column chromatography (silica gel, mobile phase 95:5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-49f3ae8e8939471ca48eb17b22f8e65b
Source dataset
uspto-grants-1988_05
Patent number
US04745111

Reaction notes

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