Ethylenediamine → HCID 12649781, compound

HRID 435756Notes

Reaction equation

HRID 435756 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][N:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][C:5]=3[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1.C(N)CN>O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[C:6]3[CH2:11][N:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 99931-Bromo-4-fluorobenzeneHCID 10340Sodium CarbonateHCID 12649780HCID 12649780, compound

Product 1

HCID 12649781HCID 12649781, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.6 g. (0.028 mole) of 7-fluoro-2-carbethoxy-1,2,3,4-tetrahydropyrrolo[3,4-b]indole, 8.86 g. (0.031 mole) of cuprous bromide, 3.28 g. (0.031 mole) of sodium carbonate and 17.2 g. (0.098 mole) of p-bromofluorobenzene in 75 ml. of N-methyl-2-pyrrolidione is heated to reflux for 4 hrs. The reaction mixture is cooled and poured into ice and water containing 40 ml. of ethylene diamine. The mixture is extracted with benzene, and the benzene extracts subsequently back-washed with water and a saturated brine solution and dried over magnesium sulfate. Removal of the solvent in vacuo provides a gum which on trituration with hexane provides 5.8 g. of product as a brown solid, m.p. 143°-145° C.

Workup

  1. additionA mixture of 6.6 g
  2. temperatureof N-methyl-2-pyrrolidione is heated
  3. temperatureto reflux for 4 hrs
  4. temperatureThe reaction mixture is cooled
  5. extractionThe mixture is extracted with benzene
  6. washthe benzene extracts subsequently back-washed with water
  7. dry with materiala saturated brine solution and dried over magnesium sulfate
  8. customRemoval of the solvent in vacuo
  9. customprovides a gum which on trituration with hexane
  10. customprovides 5.8 g

Sources & evidence

ORD record
ord-d4902f8917f04d2aa69faab7b8a76c34
Source dataset
uspto-grants-1977_02
Patent number
US04006164

Reaction notes

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