4-Methylmorpholine → HCID 68874178, compound

HRID 1986391Notes

Reaction equation

HRID 1986391 reaction equation
[OH:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>C1COCC1>[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:10](=[O:12])/[CH:9]=[CH:8]/[C:4]2[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=2)[CH2:16][CH2:15]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 6375413-coumaric acid, (E)-HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68874178HCID 68874178, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, to a solution of (2E)-3-(3-hydroxyphenyl)-2-propenoic acid (330 mg, 2.0 mmol) in THF (20 mL), was added 1-methylpiperazine (400 mg, 4.0 mmol), HOBT (810 mg, 6.0 mmol), HBTU (760 mg, 2 mmol), followed with 4-methylmorpholine (670 μL, 6.0 mmol). This mixture was then stirred at rt for overnight. The reaction mixture was concentrated and the residue was purified with reverse phase HPLC (5% MeCN/H2O→60% MeCN/H2O) to afford the title compound as a white solid (397 mg, 81%). MS (S+) m/e 247 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified with reverse phase HPLC (5% MeCN/H2O→60% MeCN/H2O)

Sources & evidence

ORD record
ord-bf8ab032ab4044208c7c00009f66b454
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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