N'-(3-(Dimethylamino)propyl)-N,N-dimethyl-1,3-propanediamine → 3-[bis-(3-dimethylamino-propyl)-carbamoyl]-acrylic Acid Ethyl Ester

HRID 1869115Notes

Reaction equation

[NH:1]([CH2:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])[CH2:2][CH2:3][CH2:4][N:5]([CH3:7])[CH3:6].[Cl-].[CH2:15]([O:17][C:18](=[O:24])/[CH:19]=[CH:20]/[C:21](O)=[O:22])[CH3:16].C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH2:15]([O:17][C:18](=[O:24])[CH:19]=[CH:20][C:21](=[O:22])[N:1]([CH2:2][CH2:3][CH2:4][N:5]([CH3:6])[CH3:7])[CH2:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])[CH3:16]

Participants

Conditions

Temperature: 23 °C

Procedure

3,3′-Iminobis(N,N-dimethyl-propylamine) (10.66 g, 55 mmol) and DMAP (54 mg) are dissolved in toluene (60 ml). To this solution is added the solution of fumaric acid monoethyl ester mono chloride (8.15 g, 50 mmol) in toluene (20 ml) over 20 min via syringe pump. The mixture is further stirred for 3 h at 23° C., then poured on a mixture of ice and sat. aq. NaHCO3-solution. The product is extracted twice with EtOAc (100 ml) and the organic layers washed twice with brine, combined and dried over MgSO4.

Workup

extractionThe product is extracted twice with EtOAc (100 ml)
washthe organic layers washed twice with brine
dry with materialdried over MgSO4

Sources & evidence

ORD record: ord-49cf0cc1745f46898cc11b10d24c5bc3
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638118B2

Reaction notes

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