1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 18388390, compound

HRID 2296819Notes

Reaction equation

HRID 2296819 reaction equation
[CH2:1]([O:3][C:4](=[O:10])/[CH:5]=[CH:6]/[C:7]([O-:9])=O)[CH3:2].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.Cl.[CH3:25][N:26]([CH3:35])[CH2:27][CH2:28][CH2:29]N=C=NCC>C(Cl)Cl>[CH2:27]([N:26]1[CH2:25][CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:10])[CH:6]([C:7]([N:21]2[CH2:20][CH2:19][CH:18]([C:15]3[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=3)[CH2:23][CH2:22]2)=[O:9])[CH2:35]1)[C:28]1[CH:29]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27591364-(4-Fluorophenyl)piperidineHCID 58782252-Butenedioic acid, monoethyl ester

Product 1

HCID 18388390HCID 18388390, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.87 g (20 mmol) of mono-ethylfumarate (Aldrich), 3.24 g (20 mmol of 4-(4-fluorophenyl)piperidine, 2.93 g (24 mmol) of 4-dimethylaminopyridinie, and 7.67 g (40 mmol) of 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride in 40 mL of CH2Cl2 at rt was stirred for 2.5 h. The reaction mixture was diluted with CH2Cl2, washed with NaHCO3, dried over Na2SO4, filtered. The filtrate was concentrated and the residue was purified by chromatography (silica, acetone: hexanes, 1:3) to give 4.4 g of the title compound 1H NMR (CDCl3) δ 7.44 (d, 1H, J=15.5 Hz), 7.14-7.16 (m, 2H), 7.00 (t, 2H, J=8.5 Hz), 6.77 (d, 1H, J=15.5 Hz), 4.26 (q, 2H, J=7 Hz), 1.33 (t, 3H, J=7 Hz).

Workup

  1. washwashed with NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography (silica, acetone: hexanes, 1:3)

Sources & evidence

ORD record
ord-8cb90af0f2604ea9a7a70f299beb1395
Source dataset
uspto-grants-2002_12
Patent number
US06489354B1

Reaction notes

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