Pyrrolidine → HCID 20335509, compound

HRID 1706432Notes

Reaction equation

HRID 1706432 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O-:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.F[C:13]1[CH:22]=[CH:21][C:20]2[N+:19]3[CH:23]=[C:24]4[CH:33]=[CH:32][C:31]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=5[N:25]4[C:18]=3[CH:17]=[CH:16][C:15]=2[CH:14]=1.[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>CN1CCCC1=O>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[N:34]1([C:13]2[CH:22]=[CH:21][C:20]3[N+:19]4[CH:23]=[C:24]5[CH:33]=[CH:32][C:31]6[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=6[N:25]5[C:18]=4[CH:17]=[CH:16][C:15]=3[CH:14]=2)[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 20335473HCID 20335473, compound

Product 1

HCID 20335509HCID 20335509, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 202 g. of 3-fluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium p-toluenesulfonate, 600 ml. of N-methyl-2-pyrrolidinone and 111 ml. of pyrrolidine is heated at reflux (158 C. ) for 45 minutes, then cooled to 0°-5° C. The resulting precipitate of 3-(1-pyrrolidinyl)-imidazo[1,2-a:3,4-a']diquinolin-15-ium p-toluenesulfonate is collected by filtration, washed with ethyl acetate, then with water, and dried; m.p. 228°-237° C.

Workup

  1. additionA mixture of 202 g
  2. temperatureat reflux (158 C. ) for 45 minutes
  3. temperaturecooled to 0°-5° C
  4. filtrationThe resulting precipitate of 3-(1-pyrrolidinyl)-imidazo[1,2-a:3,4-a']diquinolin-15-ium p-toluenesulfonate is collected by filtration
  5. washwashed with ethyl acetate
  6. dry with materialwith water, and dried

Sources & evidence

ORD record
ord-cc681d8c26034d90a21f90cfeba994d7
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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