5-Aminovaleric acid → Ethyl 5-aminopentanoate hydrochloride

HRID 1759355Notes

Reaction equation

HRID 1759355 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].[CH2:13](O)[CH3:14]>>[ClH:3].[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 3

HCID 1385-Aminovaleric acidHCID 702EthanolHCID 24386Thionyl Chloride

Product 1

HCID 16094861Ethyl 5-aminopentanoate hydrochloride

Procedure

To 100 ml of absolute ethanol, stirred under a dry nitrogen atmosphere and cooled in an ice bath, was added 12.0 ml (167 mmole) of thionyl chloride, followed by 10.0 gm (85.3 mmole) of 5-aminopentanoic acid. The mixture was heated at reflux for 18 hours, cooled and concentrated in vacuo to a sticky solid. The crude ester was triturated with 150 ml of diethyl ether, and the resultant fluffy white solid was collected, washed thoroughly with diethyl ether, and dried in vacuo over potassium hydroxide to give 14.3 gm (78.7 mmole) of ethyl 5-aminopentanoate hydrochloride. The ester was sufficiently pure according to nmr spectroscopy (in (CD3)2SO) for subsequent use without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 18 hours
  4. temperaturecooled
  5. concentrationconcentrated in vacuo to a sticky solid
  6. customThe crude ester was triturated with 150 ml of diethyl ether
  7. customthe resultant fluffy white solid was collected
  8. washwashed thoroughly with diethyl ether
  9. dry with materialdried in vacuo over potassium hydroxide

Sources & evidence

ORD record
ord-852baa3523d04d51ac559f9641cb1af1
Source dataset
uspto-grants-1982_07
Patent number
US04340730

Reaction notes

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