Pyrrolidine → HCID 86737042, compound

HRID 1706438Notes

Reaction equation

HRID 1706438 reaction equation
[I-:1].F[C:3]1[CH:12]=[CH:11][C:10]2[N+:9]3[CH:13]=[C:14]4[CH:23]=[CH:22][C:21]5[CH:20]=[C:19](F)[CH:18]=[CH:17][C:16]=5[N:15]4[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>CN1CCCC1=O>[I-:1].[N:25]1([C:3]2[CH:12]=[CH:11][C:10]3[N+:9]4[CH:13]=[C:14]5[CH:23]=[CH:22][C:21]6[CH:20]=[C:19]([N:25]7[CH2:29][CH2:28][CH2:27][CH2:26]7)[CH:18]=[CH:17][C:16]=6[N:15]5[C:8]=4[CH:7]=[CH:6][C:5]=3[CH:4]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 20335583HCID 20335583, compound

Product 1

HCID 86737042HCID 86737042, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4.41 g. of 3,10-difluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide, 9.0 ml. of pyrrolidine and 130 ml. of N-methyl-2-pyrrolidinone is stirred and heated at 130°-160° C. for 4.5 hours, then cooled. The resulting precipitate is collected, washed with methanol and stirred with 100 ml. of 2% aqueous triethylamine hydroiodide for 1 hour. The resulting precipitate of 3,10-di-(1-pyrrolidinyl)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration, washed with water and dried; m.p. 345° C. (dec.), after crystallization from dimethylformamide/-2-propanol.

Workup

  1. additionA mixture of 4.41 g
  2. temperatureheated at 130°-160° C. for 4.5 hours
  3. temperaturecooled
  4. customThe resulting precipitate is collected
  5. washwashed with methanol
  6. filtrationThe resulting precipitate of 3,10-di-(1-pyrrolidinyl)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration
  7. washwashed with water
  8. customdried
  9. customm.p. 345° C. (dec.), after crystallization from dimethylformamide/-2-propanol

Sources & evidence

ORD record
ord-bf870b108dd6403389f76d2632089b67
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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