6-Aminohexanoic Acid → ethyl 6-aminohexanoate hydrochloride

HRID 2366597Notes

Reaction equation

HRID 2366597 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].[CH2:14](O)[CH3:15]>>[ClH:3].[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 702EthanolHCID 24386Thionyl Chloride

Product 1

HCID 458476ethyl 6-aminohexanoate hydrochloride

Conditions

Temperature
-78 °C

Procedure

Anhydrous ethanol (400 mL) was cooled to −78° C., and thionyl chloride (63.34 mL, 868.4 mmol) was added. The reaction was stirred for one hour at −78° C., and solid 6-aminocaproic acid (100.0 g, 723.7 mmol) was then added. The reaction was allowed to warm to ambient temperature slowly, stirred overnight, and then concentrated under reduced pressure. The residue was recrystallized from ethyl acetate:diethyl ether to provide 137 g of ethyl 6-aminocaproate hydrochloride as a white solid.

Workup

  1. temperatureto warm to ambient temperature slowly
  2. stirringstirred overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8d56596e3f0e40f19c6ed666858a69a0
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…