Azetidine → HCID 20335467, compound

HRID 1706436Notes

Reaction equation

HRID 1706436 reaction equation
[I-:1].[CH2:2]([C:4]1[CH:13]=[CH:12][C:11]2[N+:10]3[CH:14]=[C:15]4[CH:24]=[CH:23][C:22]5[CH:21]=[C:20](F)[CH:19]=[CH:18][C:17]=5[N:16]4[C:9]=3[CH:8]=[CH:7][C:6]=2[CH:5]=1)[CH3:3].[NH:26]1[CH2:29][CH2:28][CH2:27]1>CN(C)C=O>[I-:1].[N:26]1([C:20]2[CH:19]=[CH:18][C:17]3[N:16]4[C:9]5[CH:8]=[CH:7][C:12]6[CH:13]=[C:4]([CH2:2][CH3:3])[CH:5]=[CH:6][C:11]=6[N+:10]=5[CH:14]=[C:15]4[CH:24]=[CH:23][C:22]=3[CH:21]=2)[CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 10422Azetidine2×HCID 20335595HCID 20335595, compound

Product 1

HCID 20335467HCID 20335467, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 2.21 g. of 3-ethyl-10-fluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide, 15 ml. of dimethylformamide and 1.0 ml. of azetidine is heated at 72° C. for 3 days in a pressure vessel, then cooled, treated with 0.5 ml. of azetidine and allowed to stand at 20°-25° C. for 7 days, with occasional agitation. The resulting precipitate of 10-(1-azetidinyl)-3-ethylimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration, washed with water and dried; m.p. 270°-275° C., after crystallization from methanol.

Workup

  1. additionA stirred mixture of 2.21 g
  2. temperaturecooled
  3. additiontreated with 0.5 ml
  4. filtrationThe resulting precipitate of 10-(1-azetidinyl)-3-ethylimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration
  5. washwashed with water
  6. customdried
  7. customm.p. 270°-275° C., after crystallization from methanol

Sources & evidence

ORD record
ord-0e5669d858e640e5bcc698daa8af2584
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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