4-Methylmorpholine → N-[2-(Dimethylamino)ethyl]-4-formylbenzamide

HRID 592072Notes

Reaction equation

HRID 592072 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)=[O:2].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH2:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH:16][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 120884-Formylbenzoic acidHCID 66053N,N-DimethylethylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57438695N-[2-(Dimethylamino)ethyl]-4-formylbenzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-formylbenzoic acid (24) (300 mg, 1.99 mmol) in DCM (4 mL) were added N,N-dimethylethane-1,2-diamine (193.8 mg, 2.19 mmol), HATU (911.8 mg, 2.4 mmol), NMM (505 mg, 5.0 mmol), and DMAP (24 mg, 0.199 mg) at RT. The reaction mixture was stirred at RT for 16 h. The reaction was monitored by LCMS. After 16 h, RM was washed with water and organic layer was concentrated after drying over Na2SO4. Column purification of crude material afforded pure product as oil.

Workup

  1. waitAfter 16 h
  2. washRM was washed with water and organic layer
  3. concentrationwas concentrated
  4. dry with materialafter drying over Na2SO4
  5. customColumn purification of crude material
  6. customafforded pure product as oil

Sources & evidence

ORD record
ord-ce2734ec1025482f861ba5d432e7dd28
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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