4-Methylpiperidine → HCID 20335523, compound

HRID 1706430Notes

Reaction equation

HRID 1706430 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]([CH:24]([CH3:26])[CH3:25])[CH:18]=[CH:17][C:16]=5[N:15]4[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=1.[CH3:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>CN(C)C=O>[I-:1].[CH3:25][CH:24]([C:19]1[CH:18]=[CH:17][C:16]2[N:15]3[C:8]4[CH:7]=[CH:6][C:5]5[CH:4]=[C:3]([N:31]6[CH2:32][CH2:33][CH:28]([CH3:27])[CH2:29][CH2:30]6)[CH:12]=[CH:11][C:10]=5[N+:9]=4[CH:13]=[C:14]3[CH:23]=[CH:22][C:21]=2[CH:20]=1)[CH3:26]

Participants

4

Reactant 2

HCID 693814-MethylpiperidineHCID 20335494HCID 20335494, compound

Product 1

HCID 20335523HCID 20335523, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.7 g. of 3-fluoro-10-(1-methylethyl)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide, 20 ml. of dimethylformamide and 4.0 ml. of 4-methylpiperidine is stirred and heated at reflux for 1 hour, then evaporated at reduced pressure. The residue is stirred with 75 ml. of ethyl acetate and the resulting precipitate is collected by filtration. The solid is stirred with 150 ml. of 1% aqueous triethylamine hydroiodide, collected by filtration, washed with water and dried. This product is 10-(1-methylethyl-3-(4-methyl-1-piperidinyl)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide; m.p. 266°-269° C., after crystallization from methanol/acetonitrile.

Workup

  1. additionA mixture of 4.7 g
  2. temperatureheated
  3. temperatureat reflux for 1 hour
  4. customevaporated at reduced pressure
  5. filtrationof ethyl acetate and the resulting precipitate is collected by filtration
  6. stirringThe solid is stirred with 150 ml
  7. filtrationof 1% aqueous triethylamine hydroiodide, collected by filtration
  8. washwashed with water
  9. customdried
  10. customm.p. 266°-269° C., after crystallization from methanol/acetonitrile

Sources & evidence

ORD record
ord-39114a022e904b77822996921e6fc272
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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