1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-chlorohexyl(2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoate

HRID 523328Notes

Reaction equation

HRID 523328 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH2:13]([O:15][C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])=[CH:21][CH:20]=1)=[O:17])[CH3:14].[Cl:30][CH:31](O)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:13]([O:15][C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]([O:29][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][Cl:30])=[O:28])=[CH:21][CH:20]=1)=[O:17])[CH3:14]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12768704ChlorohexanolHCID 12876666(2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoic acid

Product 1

HCID 867326476-chlorohexyl(2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoateYield 73.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

69.2 g (343 mmol) of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC hydrochloride) are added to a solution of 95.4 g (343 mmol) of (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoic acid, 4.27 g (34.3 mmol) of 4-dimethylaminopyridine in 1.5 L of dichloromethane at 0° C. To this mixture, 46.7 mL (343 mmol) of chlorohexanol in 100 mL of dichloromethane are incorporated 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 toluene yielded 89.3 g (72%) of pure 6-chlorohexyl(2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoate as a white powder.

Workup

  1. customare incorporated at 10° C
  2. customThe reaction mixture is then partitioned between dichloromethane and water
  3. washThe organic phase is washed repeatedly with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-3f2e8a10007540acafdde0e6a2faca43
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Reaction notes

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