Ethylenediamine → HCID 12891874, compound

HRID 427159Notes

Reaction equation

HRID 427159 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[C:9](Br)[CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][CH2:4]1.[CH3:18][N:19](C)C=O.C(N)CN>O>[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[C:9]([C:18]#[N:19])[CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6228DimethylformamideHCID 123618078-Bromo-N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

Product 1

HCID 12891874HCID 12891874, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(Dimethylamino)-8-bromo-1,2,3,4-tetrahydrocarbazole (18.8 g.) (Example 211) and 17.5 g. of cuprous cyanide in 150 ml. of dimethylformamide was heated under reflux for four hours. The warm reaction mixture was poured into a solution of 200 ml. of ethylenediamine in 400 ml. of water. This was mixed thoroughly and extracted several times with chloroform. The chloroform layer was separated and washed with a dilute solution of ethylenediamine, water, saturated salt solution, and evaporated to dryness to give, after recrystallization from benzene, 6.9 g. of 3-(dimethylamino)-8-cyano-1,2,3,4-tetrahydrocarbazole, m.p. 177°-179° C.

Workup

  1. temperatureunder reflux for four hours
  2. customThe warm reaction mixture
  3. additionwas poured into a solution of 200 ml
  4. additionThis was mixed thoroughly
  5. extractionextracted several times with chloroform
  6. customThe chloroform layer was separated
  7. washwashed with a dilute solution of ethylenediamine, water, saturated salt solution
  8. customevaporated to dryness
  9. customto give
  10. customafter recrystallization from benzene, 6.9 g

Sources & evidence

ORD record
ord-b3bd2ce3b4804ba19d1c95b9caae28f1
Source dataset
uspto-grants-1979_10
Patent number
US04172834

Reaction notes

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