1-Hexanol → Hexaminolevulinate hydrochloride

HRID 1296586Notes

Reaction equation

HRID 1296586 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>Cl>[ClH:1].[NH2:2][CH2:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([O:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:8]

Participants

4

Reactant 2

HCID 81031-HexanolHCID 123608Aminolevulinic Acid Hydrochloride

Product 1

HCID 6433082Hexaminolevulinate hydrochlorideYield 79.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

2 grams of 5-aminolevulinic acid hydrochloride was dissolved in 25 grams of dry n-hexanol with 5–6 drops of conc. hydrochloride added in a 50 ml glass reactor equipped with a reflux condenser and a thermometer. The reaction mixture was held at 50–60° C. for approx. 3 days. The excess n-hexanol was removed under vacuum and the product finally dried under high vacuum, giving 2.4 grams of n-hexyl 5-aminolevulinate hydrochloride. The structure was confirmed by 1H-NMR spectroscopy in DMSO-d6.

Workup

  1. additionadded in a 50 ml glass reactor
  2. customequipped with a reflux condenser
  3. customThe excess n-hexanol was removed under vacuum
  4. customthe product finally dried under high vacuum

Sources & evidence

ORD record
ord-aa719fbeb6c34daf8a538dbfbc277798
Source dataset
uspto-grants-2007_07
Patent number
US07247655B2

Reaction notes

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