Dimethylformamide → 4-Methylmorpholine

HRID 559619Notes

Reaction equation

HRID 559619 reaction equation
[CH3:1][CH2:2][CH2:3][P:4](=[O:6])=[O:5].[CH:7]1N=CN([C:12]([N:14]2[CH:18]=N[CH:16]=[CH:15]2)=O)C=1.C([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.CN([CH:29]=[O:30])C>CN1C(=O)N(C)CCC1.CC(N(C)C)=O.CN1C(=O)CCC1>[CH3:1][CH2:2][CH2:3][P:4](=[O:6])=[O:5].[CH3:12][N:14]1[CH2:18][CH2:29][O:30][CH2:16][CH2:15]1.[CH:2]([N:21]([CH:22]([CH3:23])[CH3:7])[CH2:24][CH3:25])([CH3:3])[CH3:1]

Participants

10

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 16167369Propylphosphoric anhydride

Product 3

HCID 79724-MethylmorpholineHCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydride

Reagents, catalysts & solvents 3

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 31374DimethylacetamideSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

reacting (V) with an activating agent such as propylphosphonic anhydride or CDI (N,N-carbonyldiimidazole), (preferably propylphosphonic anhydride), and an amine of the formula (VI) in the presence of an amine base such as N-methylmorpholine, triethylamine, or diisopropylethylamine, in a suitable polar aprotic solvent such as DMF, or NMP, DMAC, DMPU to provide (I), and subsequently isolating (I),

Sources & evidence

ORD record
ord-6f7afce3da2d4f96be8213050b7c5063
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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