Ethylenediamine → HCID 13715489, compound

HRID 1165868Notes

Reaction equation

HRID 1165868 reaction equation
C[Al](C)C.[CH2:5]([NH2:8])[CH2:6][NH2:7].C(O[C:12]([CH:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O)C>C1(C)C=CC=CC=1>[NH:7]1[CH2:6][CH2:5][N:8]=[C:12]1[CH:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 13869736HCID 13869736, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 13715489HCID 13715489, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirring solution of 2 molar trimethylaluminum in toluene (13.1 ml) at 10° C. under argon is added ethylenediamine (1.75 ml) dropwise under cooling to maintain a temperature of +10° C. It is allowed to warm to room temperature and then ethyl-2,3-dihydro-1-phenylindole-2-carboxylate (3.5 g) in toluene (15 ml) is added under argon. The whole is heated gradually to reflux and maintained at this temperature under argon for 18 hours. This cooled mixture is quenched in water (40 ml) and treated with methanol (40 ml) and methylene chloride (40 ml). The aqueous layer is separated and extracted further with methylene chloride (3×100 ml). The combined organic extracts are dried over sodium sulfate and concentrated to dryness at reduced pressure. The residue is dissolved in boiling ethyl acetate (150 ml), filtered through sodiumsulfate and concentrated to reduced pressure to a small volume from which yellow solid precipitates. The pure dl-2,3-dihydro-2-(4,5-dihydroimidazol-2-yl)-1-phenylindole, mp. 141°- 144°, is thus obtained.

Workup

  1. temperatureunder cooling
  2. temperatureto maintain a temperature of +10° C
  3. temperatureThe whole is heated gradually
  4. temperatureto reflux
  5. temperaturemaintained at this temperature under argon for 18 hours
  6. customThis cooled mixture is quenched in water (40 ml)
  7. additiontreated with methanol (40 ml) and methylene chloride (40 ml)
  8. customThe aqueous layer is separated
  9. extractionextracted further with methylene chloride (3×100 ml)
  10. dry with materialThe combined organic extracts are dried over sodium sulfate
  11. concentrationconcentrated to dryness at reduced pressure
  12. dissolutionThe residue is dissolved
  13. filtrationfiltered through sodiumsulfate
  14. concentrationconcentrated to reduced pressure to a small volume from which yellow solid
  15. customprecipitates

Sources & evidence

ORD record
ord-417740e3b8e642599353f83cb03e4650
Source dataset
uspto-grants-1990_03
Patent number
US04912125

Reaction notes

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