Ammonia → 1-(2-Chlorophenyl)-3-(2-aminopropyl)indole

HRID 1606509Notes

Reaction equation

HRID 1606509 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C:18](=[N:20]O)[CH3:19])=[CH:9]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].N>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH:18]([NH2:20])[CH3:19])=[CH:9]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 21226445Aluminium lithium hydrideHCID 539360231-(2-Chlorophenyl)-3-(2-hydroxyiminopropyl)indole

Product 1

HCID 215434941-(2-Chlorophenyl)-3-(2-aminopropyl)indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.052 mole of 1-(2-chlorophenyl)-3-(2-hydroxyiminopropyl)indole is dissolved in 150 ml of dry tetrahydrofuran. 6 gms of lithium aluminium hydride are slowly added whilst refluxing for 3.5 hours. The reaction mixture is then poured on to a mixture of ice and ammonia and the product extracted with ether. The ethereal extract is treated with an N hydrochloric acid solution. The latter is then rendered alkaline with N soda solution. The turbid substance formed is extracted with ether, washed with water and dried. On removing the solvent the primary amine is obtained which, after recrystallisation from di-isopropyl ether, had a melting point of 79°C.

Workup

  1. temperaturewhilst refluxing for 3.5 hours
  2. extractionthe product extracted with ether
  3. extractionThe ethereal extract
  4. additionis treated with an N hydrochloric acid solution
  5. customThe turbid substance formed
  6. extractionis extracted with ether
  7. washwashed with water
  8. customdried
  9. customOn removing the solvent the primary amine
  10. customis obtained which
  11. customafter recrystallisation from di-isopropyl ether

Sources & evidence

ORD record
ord-fa8c8ed403c24d4ca0e625101526634f
Source dataset
uspto-grants-1976_04
Patent number
US03953442

Reaction notes

Loading…