Citric Acid → 1-(Azepan-1-yl)-2-chloroethan-1-one

HRID 1950313Notes

Reaction equation

HRID 1950313 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[Cl:8][CH2:9][C:10](Cl)=[O:11].[C:13](O)(=O)[CH2:14]C(CC(O)=O)(C(O)=O)O>O1CCCC1>[N:3]1([C:10](=[O:11])[CH2:9][Cl:8])[CH2:4][CH2:5][CH2:14][CH2:13][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 6577Chloroacetyl chlorideHCID 8471Triethylamine

Product 1

HCID 31441341-(Azepan-1-yl)-2-chloroethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of hexamethyleneimine (2.9 ml) in tetrahydrofuran (25 ml) was added triethylamine (3.5 ml). Chloroacetyl chloride (2.0 ml) was added thereto on an ice bath followed by stirring for 1.5 hours while warming to room temperature. An aqueous solution of 10% citric acid was added thereto, the solution was extracted with ethyl acetate, then sequentially washed with a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (3.5 g).

Workup

  1. customon an ice bath followed
  2. extractionthe solution was extracted with ethyl acetate
  3. washsequentially washed with a saturated aqueous solution of sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-a3c3867b86914b15975800fa51eb188c
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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