Morpholine → 4-(6-Chloropyridine-3-carbonyl)morpholine

HRID 601001Notes

Reaction equation

HRID 601001 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:7])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 8574994-(6-Chloropyridine-3-carbonyl)morpholineYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6-chloro-nicotinoyl chloride (0.540 g, 3.07 mmoles) in dichloromethane (10 mL) was added of morpholine, (0.294 g, 1.1 equivalents) followed by triethylamine (940 uL, 2.2 equivalents). The reaction was stirred overnight at room temperature to give (6-chloro-pyridin-3-yl)-morpholin-4-yl-methanone. No starting material, 6-Chloro-nicotinoyl chloride, remained and mass spectrometry showed correct M+ ion. An aqueous work-up was performed and the crude material was taken to the next step. The crude residue, (6-chloro-pyridin-3-yl)-morpholin-4-yl-methanone, weighed 0.610 g (88% yield) after aqueous work-up.

Sources & evidence

ORD record
ord-25f69ff54db3402eaf13603e76dac3fa
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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