Benzene → HCID 20327584, compound

HRID 372456Notes

Reaction equation

HRID 372456 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]=1)(=O)[CH3:2].C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>O>[CH3:2][C:1]1[C:8]2[N:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][N:4]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

5

Reactant 3

HCID 241BenzeneHCID 24813Phosphorus oxychlorideHCID 20327585HCID 20327585, compound

Product 1

HCID 20327584HCID 20327584, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 40.8 g. N-acetyl-1-phenyltryptamine (IIIa), 800 ml. dry benzene and 220 g. phosphorus oxychloride is refluxed for 1 hour. After cooling, the reaction mixture is poured into two liters of cold water with continued stirring and cooling for 1.5 hours. The organic layer is separated, washed twice with water and the aqueous fractions combined and backwashed once with ethyl acetate. The aqueous extract (total volume 3 liters) is treated with one liter of 10% NaOH, followed by one liter of 50% NaOH while stirring and cooling in an ice bath. The product precipitates from the cooled solution and is filtered and washed well with water to remove any co-precipitated inorganic material. Upon drying, 34 g. of 4,9-dihydro-1-methyl-9-phenyl-3H-pyrido[3,4-b]indole, (IVa), m.p. 110°-112° C. is obtained. An analytical sample had a m.p. 110°-112° C. (benzene-petroleum ether).

Workup

  1. additionA mixture of 40.8 g
  2. temperatureAfter cooling
  3. temperaturecooling for 1.5 hours
  4. customThe organic layer is separated
  5. washwashed twice with water
  6. extractionThe aqueous extract (total volume 3 liters)
  7. additionis treated with one liter of 10% NaOH
  8. stirringwhile stirring
  9. temperaturecooling in an ice bath
  10. customThe product precipitates from the cooled solution
  11. filtrationis filtered
  12. washwashed well with water
  13. customto remove any co-precipitated inorganic material
  14. customUpon drying

Sources & evidence

ORD record
ord-ce30659538074c178a2fca670dd551ff
Source dataset
uspto-grants-1978_05
Patent number
US04091102

Reaction notes

Loading…