2-Pyrrolidone → HCID 13491600, compound

HRID 1284922Notes

Reaction equation

HRID 1284922 reaction equation
P(Cl)(Cl)(Cl)=O.[NH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=O.[CH3:12][N:13]1[CH2:25][CH:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:16]2=[CH:17][CH:18]=[C:19]3[C:23]([NH:22][CH2:21][CH2:20]3)=[C:15]2[CH2:14]1>C1(C)C=CC=CC=1.C(Cl)Cl>[N:6]1([N:22]2[C:23]3[C:19](=[CH:18][CH:17]=[C:16]4[CH:24]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:25][N:13]([CH3:12])[CH2:14][C:15]4=3)[CH2:20][CH2:21]2)[CH2:10][CH2:9][CH:8]=[CH:7]1

Participants

6

Reactant 3

HCID 120252-PyrrolidoneHCID 24813Phosphorus oxychlorideHCID 13491595HCID 13491595, compound

Product 1

HCID 13491600HCID 13491600, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.9 ml (0.02 mol) of phosphorus oxychloride in 6 ml of toluene is added dropwise to a solution of 3.4 g (0.04 mol) of pyrrolid-2-one in 8 ml of toluene at a temperature between 2° and 0° C., with stirring and cooling. The mixture is stirred at room temperature for 11/2 hours and left to stand overnight. A solution of 5.2 g (0.02 mol) of 8-methyl-6-phenyl-2,3,6,7,8,9-hexahydro-1H-pyrido[4,3-g]indole in 10 ml of toluene and 20 ml of CH2Cl2 is then added. The CH2Cl2 is distilled off and the reaction mixture is stirred at a temperature between 75° and 80° C. for 8 hours, with stirring. The solid which has precipitated is filtered off with suction, and 2N NaOH and H2O are added in order to convert it into the free base. The aqueous phase is extracted with CH2Cl2, the CH2Cl2 phase is dried and the solvent is removed. The residue is chromatographed on silica gel 60 from E. Merck, Darmstadt) using an eluent mixture of CH2Cl2 /MeOH (2:1), and on aluminum oxide (aluminum oxide 90 from E. Merck, Darmstadt) using an eluent mixture of CH2Cl2 and MeOH (20:0.25). The product is dried in a desiccator over P2O5 under a water pump vacuum.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at room temperature for 11/2 hours
  3. waitleft
  4. distillationThe CH2Cl2 is distilled off
  5. stirringthe reaction mixture is stirred at a temperature between 75° and 80° C. for 8 hours
  6. stirringwith stirring
  7. customThe solid which has precipitated
  8. filtrationis filtered off with suction, and 2N NaOH and H2O
  9. additionare added in order
  10. extractionThe aqueous phase is extracted with CH2Cl2
  11. dry with materialthe CH2Cl2 phase is dried
  12. customthe solvent is removed
  13. customThe residue is chromatographed on silica gel 60 from E
  14. additionan eluent mixture of CH2Cl2 /MeOH (2:1)
  15. additionan eluent mixture of CH2Cl2 and MeOH (20:0.25)
  16. dry with materialThe product is dried in a desiccator over P2O5 under a water pump vacuum

Sources & evidence

ORD record
ord-c2f9e183ad6d4097ac5618a10b302287
Source dataset
uspto-grants-1986_01
Patent number
US04564613

Reaction notes

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