Morpholine → HCID 10290980, compound

HRID 396954Notes

Reaction equation

HRID 396954 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]([CH2:18][CH:19]([CH3:21])[CH3:20])[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:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[CH3:20][CH:19]([CH3:21])[CH2:18][N:5]1[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]=[C:4]1[CH2:3][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 10268183HCID 10268183, compound

Product 1

HCID 10290980HCID 10290980, compoundYield 68%

Procedure

2-Chloromethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride (Example 10, prepared from 2.0 g of the corresponding alcohol) was added to morpholine (5 mL). The mixture was refluxed for 4 hr. The resulting solution was cooled to room temperature. A solid precipitated. The solid was filtered from the mixture and slurried in aqueous sodium bicarbonate solution. The product was filtered from the mixture, washed with water, and dried to yield 1.7 g (68.0%) of solid, which was recrystallized from ethanol to give a pure product m.p. 228-234° C. Analysis: Calculated: C, 67.2; H, 7.4; N, 20.6. Found: C, 67.3; H, 7.9; N, 20.6.

Workup

  1. temperatureThe mixture was refluxed for 4 hr
  2. customA solid precipitated
  3. filtrationThe solid was filtered from the mixture
  4. filtrationThe product was filtered from the mixture
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e5d2b59f6dff48af8cf4b701ae8128f0
Source dataset
uspto-grants-2003_08
Patent number
US06608201B2

Reaction notes

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