Morpholine → HCID 69506816, compound

HRID 2366599Notes

Reaction equation

HRID 2366599 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](O)=[O:23])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C(Cl)(=O)C(Cl)=O.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>ClCCl>[N:31]1([C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:5]2[C:6]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]=[CH:8][C:7]=3[N:16]=[C:4]2[CH2:1][CH2:2][CH3:3])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 65578Oxalyl chlorideHCID 57447019HCID 57447019, compound

Product 1

HCID 69506816HCID 69506816, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanoic acid (3.0 g, 9.2 mmol) in anhydrous dichloromethane (50 mL) was cooled to 0° C. Oxalyl chloride (1.44 mL, 16.6 mmol) was added dropwise over a period of 15 minutes. The resulting solution was allowed to warm to ambient temperature and stirred for one hour and then concentrated under reduced pressure. The residue was dissolved in dichloromethane (50 mL), and morpholine (2.41 mL, 27.6 mmol) was added. The reaction was stirred overnight, washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 3.6 g of 1-(6-morpholin-4-yl-6-oxohexyl)-2-propyl-1H-imidazo[4,5-c]quinoline.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. stirringThe reaction was stirred overnight
  4. washwashed sequentially with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc980f4b356247149f21225129fc7b0c
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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