Piperidine → HCID 20335479, compound

HRID 1706425Notes

Reaction equation

HRID 1706425 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]([CH2:24][CH2:25][CH3:26])[CH:18]=[CH:17][C:16]=5[N:15]4[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=1.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>CN(C)C=O>[I-:1].[N:27]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]([CH2:24][CH2:25][CH3:26])[CH:18]=[CH:17][C:16]=6[N:15]5[C:8]=4[CH:7]=[CH:6][C:5]=3[CH:4]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 20335471HCID 20335471, compound

Product 1

HCID 20335479HCID 20335479, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 3.62 g. of 3-fluoro-10-propylimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide, 20 ml. of dimethylformamide and 2.0 ml. of piperidine is heated at 72° C. for 94 hours, then evaporated at reduced pressure. The residue is dissolved in methanol along with 2.0 g. of triethylamine hydroiodide. The solution is diluted with water and the resulting precipitate is collected by filtration and suspended in 125 ml. of 0.5% triethylamine hydroiodide. The solid 3-(1-piperidinyl)-10-propylimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration, triturated with 2-propanol and dried; m.p. 148°-153° C.

Workup

  1. additionA stirred mixture of 3.62 g
  2. customevaporated at reduced pressure
  3. dissolutionThe residue is dissolved in methanol along with 2.0 g
  4. additionThe solution is diluted with water
  5. filtrationthe resulting precipitate is collected by filtration
  6. filtrationThe solid 3-(1-piperidinyl)-10-propylimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration
  7. customtriturated with 2-propanol
  8. customdried

Sources & evidence

ORD record
ord-a40620985e894b9496b4efe9dd9c4b2b
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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