4-Methylmorpholine → HCID 68802054, compound

HRID 924625

Reaction equation

HRID 924625 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[C:5]([CH3:10])([CH3:9])[C:6]([OH:8])=O)[CH3:2].[NH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>O1CCCC1>[CH2:1]([O:3][C:4](=[O:11])[C:5]([CH3:10])([CH3:9])[C:6]([NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:8])[CH3:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2317543-Ethoxy-2,2-dimethyl-3-oxopropanoic acidHCID 4082852-MorpholinoethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 68802054HCID 68802054, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

19 g 2,2-Dimethyl-malonic acid monoethyl ester were weighed into a round-bottomed flask and under N2 atmosphere and room temperature, 200 ml tetrahydrofurane, 15.6 ml 4-(2-Aminoethyl)-morpholine and 32.6 ml N-Methylmorpholine were added. The reaction was stirred and cooled down to 5° C. Then, 43.8 g TBTU were added and the mixture was allowed to stir for another 1.5 hours. Finally the solvent was removed and the residue dissolved in 400 ml dichloromethane. This organic phase was washed two times with 500 ml NaHCO3 solution. The dichloromethane phase was dried then the solvent was evaporated. Purity of the product was judged by gas chromatography.

Workup

  1. stirringto stir for another 1.5 hours
  2. customFinally the solvent was removed
  3. dissolutionthe residue dissolved in 400 ml dichloromethane
  4. washThis organic phase was washed two times with 500 ml NaHCO3 solution
  5. dry with materialThe dichloromethane phase was dried
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-457a9135c9e34ee6b321e781a6b88108
Source dataset
uspto-grants-2016_03
Patent number
US09283186B2

Linked notes

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