Morpholine → (6-Aminopyridin-3-yl)(morpholino)methanone

HRID 1916072Notes

Reaction equation

HRID 1916072 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][N:31]=1>C(O)C>[NH2:29][C:30]1[N:31]=[CH:32][C:33]([C:34]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:35])=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 184966-Aminonicotinic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 59259223(6-Aminopyridin-3-yl)(morpholino)methanoneYield 34.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of morpholine (9.00 g, 103 mmol) in 400 mL ethanol was added N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (10.0 g, 52.2 mmol), 1-hydroxybenzotriazole (7.00 g, 51.8 mmol), and 6-aminonicotinic acid (6.00 g, 43.4 mmol). After stirring for 18 hours, the resulting solid was filtered. This was triturated with a mixture of 100 mL methanol and 100 mL dichloromethane to yield (6-Amino-pyridin-3-yl)-morpholin-4-yl-methanone (3.08 g, 14.9 mmol). MS (ESI) 208.1 (M+H)+.

Workup

  1. filtrationthe resulting solid was filtered
  2. customThis was triturated with a mixture of 100 mL methanol and 100 mL dichloromethane

Sources & evidence

ORD record
ord-e53056bae74146908979b6df4d74a62e
Source dataset
uspto-grants-2013_12
Patent number
US08618098B2

Reaction notes

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