Water → Ethyl 2-(3-chloropropylamino)isobutyrate

HRID 1600540Notes

Reaction equation

HRID 1600540 reaction equation
Cl.[NH2:2][C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].[Cl:17][CH2:18][CH2:19][CH2:20]I.O>CN(C=O)C>[Cl:17][CH2:18][CH2:19][CH2:20][NH:2][C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 813631-Chloro-3-iodopropaneHCID 22343822Ethyl 2-amino-2-methylpropanoate hydrochloride

Product 1

HCID 21829920Ethyl 2-(3-chloropropylamino)isobutyrateYield 102.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl aminoisobutyrate hydrochloride (10 g) in DMF (50 mL) was cooled to 0° C. To the solution were added potassium carbonate (18 g) and 1-chloro-3-iodopropane (12 g), and the mixture was stirred overnight at 0° C. to room temperature. Water was added to the reaction solution and the mixture was extracted with ethyl acetate toluene organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 12.5 g of crude ethyl 2-(3-chloropropylamino)isobutyrate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate toluene organic layer
  2. washwas washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9485af2431894a70aae94cc178098f47
Source dataset
uspto-grants-1999_11
Patent number
US05977027

Reaction notes

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