Hydrochloric Acid → (E)-2-(dimethylamino)ethyl dec-2-enoate

HRID 878859

Reaction equation

HRID 878859 reaction equation
[C:1]([OH:12])(=[O:11])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:13][N:14]([CH2:16][CH2:17]O)[CH3:15].Cl.CN(C)CCCN=C=NCC.Cl>ClCCl>[C:1]([O:12][CH2:17][CH2:16][N:14]([CH3:15])[CH3:13])(=[O:11])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79022-(Dimethylamino)ethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5282724trans-2-Decenoic acid

Product 1

HCID 56963173(E)-2-(dimethylamino)ethyl dec-2-enoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

trans-2-Decenoic acid (170 mg, 1 mmol) and N,N-dimethylaminoethanol (90 mg, 1 mmol) were dissolved in anhydrous dichloromethane (10 ml) and, under stirring in an ice bath, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (211 mg, 1.1 mmol) (Sigma-Aldrich) was added thereto. After stirring in an ice bath for 1 hour and then at room temperature for 8 hours, the reaction solution was poured over a diluted hydrochloric acid solution followed by extracting with chloroform. The chloroform layer was concentrated to give the aimed compound as a light brown oily product.

Workup

  1. stirringAfter stirring in an ice bath for 1 hour
  2. extractionby extracting with chloroform
  3. concentrationThe chloroform layer was concentrated

Sources & evidence

ORD record
ord-99dae69f5df3499080706f1cbe74beab
Source dataset
uspto-grants-2015_03
Patent number
US08987486B2

Linked notes

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