Morpholine → HCID 10109891, compound

HRID 396962Notes

Reaction equation

HRID 396962 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:16])[C:7]=2[N:17]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[O:28]1[CH2:29][CH2:30][N:25]([CH2:3][C:4]2[N:5]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:6]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]=[C:8]([NH2:16])[C:7]=3[N:17]=2)[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 69878366HCID 69878366, compound

Product 1

HCID 10109891HCID 10109891, compound

Procedure

2-Chloromethyl-1-phenylmethyl-1H-imidazo-[4,5-c]quinolin-4-amine hydrochloride (Example 28, prepared from 2.0 g of the alcohol) was added to morpholine (5.0 mL) and the mixture was refluxed for 4 hr. The mixture was then cooled to room temperature and the solid was filtered from the mixture. The solid was slurried in aqueous sodium bicarbonate solution, filtered from the mixture, and dried. A crude yield of 2.0 g of product as a white solid was obtained. The crude product was recrystallized from methanol/dichloromethane. m.p. >300° C. Analysis: Calculated: C, 70.7; H, 6.2; N, 18.8. Found: C, 70.4; H, 6.2; N, 18.6.

Workup

  1. temperaturethe mixture was refluxed for 4 hr
  2. filtrationthe solid was filtered from the mixture
  3. filtrationfiltered from the mixture
  4. customdried
  5. customA crude yield of 2.0 g of product as a white solid was obtained
  6. customThe crude product was recrystallized from methanol/dichloromethane

Sources & evidence

ORD record
ord-9a47694cd35741ca9fc63f828958fdf4
Source dataset
uspto-grants-2003_08
Patent number
US06608201B2

Reaction notes

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