Morpholine → HCID 57447028, compound

HRID 2366613Notes

Reaction equation

HRID 2366613 reaction equation
[N:1]1([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.C(Cl)(=O)C(Cl)=O.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>>[N:28]1([C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][N:1]2[C:13]3[C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[N:6]=[CH:5][C:4]=3[N:3]=[CH:2]2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

4

Reactant 3

HCID 8083Morpholine2×HCID 65578Oxalyl chloride2×HCID 57447027HCID 57447027, compound

Product 1

HCID 57447028HCID 57447028, compoundYield 100%

Procedure

6-(1H-Imidazo[4,5-c]quinolin-1-yl)hexanoic acid (2.5 g, 8.8 mmol) was treated with oxalyl chloride (1.39 mL, 15.9 mmol) and morpholine (2.31 mL, 26.5 mmol) according to a modification of the method described in Part F of Example 6. The reaction with oxalyl chloride was carried out at ambient temperature, and the reaction with morpholine was complete after one hour. Following the work-up procedure, 3.1 g of 1-(6-morpholin-4-yl-6-oxohexyl)-1H-imidazo[4,5-c]quinoline were obtained.

Workup

  1. customwas carried out at ambient temperature

Sources & evidence

ORD record
ord-9a09e3ed4d054926924ab4bcda385bcd
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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