Morpholine → HCID 14369768, compound

HRID 1381914Notes

Reaction equation

HRID 1381914 reaction equation
[N:1]1([CH2:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=O)=[CH:13][CH:12]=2)[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[N:1]1([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:17])=[CH:20][CH:21]=2)[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 14369747HCID 14369747, compound

Product 1

HCID 14369768HCID 14369768, compound

Conditions

Temperature
150 °C

Procedure

A suspension of ethyl 4-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)benzoate (0.50 g, 0.0018 mol) in morpholine (10 ml) was maintained at 150° C. in a bomb calorimeter for 3 days. The morpholine was evaporated off under reduced pressure to yield a crude product which was purified by column chromatography (silica gel, 10% ethanol in chloroform) and recrystallized from diethyl ether-ethyl acetate to yield [4-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone as a colorless crystalline solid, having a melting point of 188°-190° C. and the following physical characteristics:

Workup

  1. customThe morpholine was evaporated off under reduced pressure
  2. customto yield a crude product which
  3. customwas purified by column chromatography (silica gel, 10% ethanol in chloroform)
  4. customrecrystallized from diethyl ether-ethyl acetate

Sources & evidence

ORD record
ord-957d6f5f9edf42c7bafcd4f6228aac8e
Source dataset
uspto-grants-1989_02
Patent number
US04804658

Reaction notes

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