Hydrochloric Acid → 1-Butylpentyl 2-(4-acetamido-butyryl)-5-chlorohydrocinnamate

HRID 1639360Notes

Reaction equation

HRID 1639360 reaction equation
Cl.[C:2]([N:5]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[C:10]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:9]=2[CH2:8][CH2:7][C:6]1=[O:21])(=[O:4])[CH3:3].[CH3:22][CH2:23][CH2:24][CH2:25][CH:26]([OH:31])[CH2:27][CH2:28][CH2:29][CH3:30]>C(Cl)Cl>[C:2]([NH:5][CH2:14][CH2:13][CH2:12][C:11]([C:10]1[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:9]=1[CH2:8][CH2:7][C:6]([O:31][CH:26]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:25][CH2:24][CH2:23][CH3:22])=[O:21])=[O:15])(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12202Nonan-5-olHCID 198331174-Acetyl-11-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione

Product 1

HCID 198389411-Butylpentyl 2-(4-acetamido-butyryl)-5-chlorohydrocinnamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15 ml of concentrated hydrochloric acid are added to a solution of 10.00 g (0.034 mol) of 4-acetyl-11-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione in 90 ml of 5-nonanol and 50 ml of methylene chloride and the mixture is stirred at room temperature for 18 hours. The solution is concentrated, extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Chromatography on silica gel with ethyl acetate gives 1-butylpentyl 2-(4-acetamido-butyryl)-5-chlorohydrocinnamate as a yellow oil.

Workup

  1. concentrationThe solution is concentrated
  2. extractionextracted with methylene chloride/water
  3. dry with materialdried with magnesium sulfate
  4. distillationthe solvent is distilled in a vacuum

Sources & evidence

ORD record
ord-1e31c9b936514857abb46600f2c7a764
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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