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

HRID 1179210Notes

Reaction equation

HRID 1179210 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-8c4288fd37e9493f955af7d2b00c086e
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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