1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86732649, compound

HRID 523330Notes

Reaction equation

HRID 523330 reaction equation
Cl.CN(C)CCCN=C=NCC.[OH:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Cl:31])=[O:23])=[CH:16][CH:15]=1.[CH3:32][O:33][CH2:34][CH2:35][O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[CH:39][CH:38]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:32][O:33][CH2:34][CH2:35][O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41]([O:13][C:14]2[CH:15]=[CH:16][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Cl:31])=[O:23])=[CH:18][CH:19]=2)=[O:42])=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 64855624-(2-Methoxyethoxy)benzoic acidHCID 867326486-chlorohexyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate

Product 1

HCID 86732649HCID 86732649, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3 g (15 mmol) of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC hydrochloride) are added to a solution of 3.1 g (15 mmol) of 6-chlorohexyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate, 0.186 g (1.5 mmol) of 4-dimethylaminopyridine in 70 mL of dichloromethane at 0° C. To this mixture, 5.1 g (15 mmol) of 4-(2-methoxyethoxy)benzoic acid in 40 mL of dichloromethane are added at 10° C. The solution is allowed to stir at room temperature for 22 hours. The reaction mixture is then partitioned between dichloromethane and water. The organic phase is washed repeatedly with water, dried over sodium sulphate, filtered and concentrated by rotary evaporation. Chromatography of the residue using cyclohexane: ethylacetate 4:1 yielded 5.3 g (73%) of pure 4-{(1E)-3-[(6-chlorohexyl)oxy]-3-oxoprop-1-enyl}phenyl 4-(2-methoxyethoxy)benzoate as a white powder.

Workup

  1. customThe reaction mixture is then partitioned between dichloromethane and water
  2. washThe organic phase is washed repeatedly with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-0cdef7fd4d134af093d5932b33e027fd
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Reaction notes

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