Sulfuric Acid → HCID 11172701, compound

HRID 652474Notes

Reaction equation

HRID 652474 reaction equation
S(=O)(=O)(O)O.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][NH:16][CH2:17][CH:18](O)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:7]1>>[C:19]1([CH:18]2[C:7]3[NH:6][C:14]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=4[C:8]=3[CH2:15][NH:16][CH2:17]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 1118Sulfuric Acid2×HCID 13921582HCID 13921582, compound

Product 1

HCID 11172701HCID 11172701, compound

Conditions

Temperature
0 °C

Procedure

Concentrated sulfuric acid (72 mL) was stirred and cooled to 0° C. in an ice-methanol bath. α-[(1H-indol-3-ylmethyl-amino)methyl]benzyl alcohol, 22.5 g (0.08 mol) was added in small portions to the stirred cooled sulfuric acid reaction mixture over 2 hours. The cooling bath was removed and the reaction was stirred at room temperature for 5 hours. Then the reaction mixture was poured onto crushed ice, basified with 50% aqueous sodium hydroxide solution (with ice cooling). Ethyl acetate was added and the basic mixture stirred well until two clear phases resulted. The aqueous phase was extracted several more times with ethyl acetate, the combined extracts washed with water and dried over anhydrous sodium sulfate. The extract after filtration was evaporated in vacuo and the residue dissolved in hot benzene, filtered hot and allowed to crystallize to obtain 10.0 g of 2,3,4,5-tetrahydro-4-phenyl-1H-pyrido[4,3-b]indole, m.p. 135°-155° C.

Workup

  1. temperaturecooled
  2. customThe cooling bath was removed
  3. additionThen the reaction mixture was poured
  4. customonto crushed ice
  5. additionEthyl acetate was added
  6. stirringthe basic mixture stirred well until two clear phases
  7. customresulted
  8. extractionThe aqueous phase was extracted several more times with ethyl acetate
  9. washthe combined extracts washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. extractionThe extract
  12. filtrationafter filtration
  13. customwas evaporated in vacuo
  14. dissolutionthe residue dissolved in hot benzene
  15. filtrationfiltered hot
  16. customto crystallize

Sources & evidence

ORD record
ord-e4ff3f16b2d04b558d0fd7b8bfea69eb
Source dataset
uspto-grants-1987_06
Patent number
US04672117

Reaction notes

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