Ammonium Hydroxide → HCID 20299751, compound

HRID 1733500Notes

Reaction equation

HRID 1733500 reaction equation
[ClH:1].C[O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][N:12]([CH2:24][CH2:25][CH3:26])[CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH:7]=[CH:8][CH:9]=1.[OH-].[NH4+]>O>[ClH:1].[NH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([CH2:14][CH2:13][N:12]([CH2:24][CH2:25][CH3:26])[CH2:11][CH2:10][C:6]2[CH:5]=[C:4]([OH:3])[CH:9]=[CH:8][CH:7]=2)=[CH:16]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 20299766HCID 20299766, compound

Product 1

HCID 20299751HCID 20299751, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
220 °C

Procedure

The product of Step C was empasted with 50 ml of water and an excess of ammonium hydroxide was added thereto. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness. The 11.55 g of orange oil residue were added to 45 g of pyridine and the mixture was refluxed at 220° C. under an inert atmosphere for 135 minutes. The mixture was cooled to 20° C. and was made alkaline with ammonium hydroxide. The mixture was then extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness. The 12.8 g of reddish oil residue were dissolved in 60 ml of isopropanol and an excess of ethyl acetate saturated with hydrogen chloride was added thereto. The ethyl acetate was distilled and crystallization was induced after which the mixture was held overnight in a refrigerator. The mixture was vacuum filtered and the recovered product was washed with isopropanol and dried to obtain 9.3 g of 3-[2-({2-(1H-indol-3-yl)-ethyl}-propylamino)-ethyl]-phenol hydrochloride in the form of a clear beige solid melting at 192° C., then 197° C. Crystallization of the product from ethanol yielded a product melting at 198° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with water
  3. customdried
  4. customevaporated to dryness
  5. additionThe 11.55 g of orange oil residue were added to 45 g of pyridine
  6. temperatureThe mixture was cooled to 20° C.
  7. extractionThe mixture was then extracted with ethyl acetate
  8. washthe organic phase was washed with water
  9. customdried
  10. customevaporated to dryness
  11. dissolutionThe 12.8 g of reddish oil residue were dissolved in 60 ml of isopropanol
  12. additionan excess of ethyl acetate saturated with hydrogen chloride was added
  13. distillationThe ethyl acetate was distilled
  14. customcrystallization
  15. filtrationfiltered
  16. washthe recovered product was washed with isopropanol
  17. customdried

Sources & evidence

ORD record
ord-7916cc4d5d1e46b9a78b8573ce21af7d
Source dataset
uspto-grants-1980_12
Patent number
US04242355

Reaction notes

Loading…