3-Morpholino-1-propanol → Methyl 3-morpholin-4-ylpropyl (2E)but-2-ene-1,4-dioate

HRID 623354

Reaction equation

HRID 623354 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O-])=[O:5].Cl.C(N=C=NCCCN(C)C)C.[N:22]1([CH2:28][CH2:29][CH2:30][OH:31])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>ClCCl>[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O:31][CH2:30][CH2:29][CH2:28][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:5]

Participants

5

Reactant 3

HCID 1995763-Morpholino-1-propanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21721168(E)-4-methoxy-4-oxobut-2-enoate

Product 1

HCID 71711669Methyl 3-morpholin-4-ylpropyl (2E)but-2-ene-1,4-dioate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Monomethyl fumarate (MMF) was reacted with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDAC) (1.2 eq) in dichloromethane (DCM) at ca. 0° C. 3-Morpholin-4-yl-propan-1-ol (1 eq) and 4-N,N-dimethylaminopyridine (DMAP) (catalytic amount) were added to the activated carboxylic acid. After the completion of the reaction, followed by the work-up of the reaction mixture, the title compound was isolated as a viscous-oil.

Workup

  1. customAfter the completion of the reaction

Sources & evidence

ORD record
ord-23bb60e66f7149aabb84ae4d79433115
Source dataset
uspto-grants-2016_04
Patent number
US09302977B2

Linked notes

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