Hydrochloric Acid → 1-Benzylazepan-3-one

HRID 12064Notes

Reaction equation

HRID 12064 reaction equation
CC([O-])(C)C.[K+].[CH2:7]([N:14]([CH2:22]C(OCC)=O)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C1(C)C=CC=CC=1>[CH2:7]([N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[CH2:22]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 686801515-(Benzyl-ethoxycarbonylmethyl-amino)-pentanoic acid

Product 1

HCID 151522641-Benzylazepan-3-oneYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A suspension of potassium tert-butylate (336 mg) in toluene (2.5 ml) is refluxed for 10 min. Then 5-(benzyl-ethoxycarbonylmethyl-amino)-pentanoic acid (695 mg) in toluene (1 ml) is slowly added to the suspension and when the addition is complete the mixture is refluxed for another 1.5 hours. After cooling to room temperature 25% hydrochloric acid (1 ml) is added. The organic phase is separated off and washed with 25% hydrochloric acid (4×1 ml). The combined hydrochloric-acid aqueous phases are then refluxed for 5 hours. After cooling to room temperature the solution is made alkaline (pH 11) with 2N caustic soda solution and extraction is carried out with ethyl acetate. The combined organic phases are concentrated by evaporation after drying over sodium sulphate. The obtained residue produces, after chromatography using silica gel (ethyl acetate/heptane 1:5) the desired title compound (197 mg) in a yield of 45% (Bull. Chem. Soc. Jpn. 1956, 29, 631-632; DE2206385).

Workup

  1. temperatureis refluxed for 10 min
  2. additionthe addition
  3. temperatureis refluxed for another 1.5 hours
  4. additionis added
  5. customThe organic phase is separated off
  6. washwashed with 25% hydrochloric acid (4×1 ml)
  7. temperatureThe combined hydrochloric-acid aqueous phases are then refluxed for 5 hours
  8. extractionwith 2N caustic soda solution and extraction
  9. concentrationThe combined organic phases are concentrated by evaporation
  10. dry with materialafter drying over sodium sulphate
  11. customThe obtained residue produces

Sources & evidence

ORD record
ord-4e89e4efeb0e4d1989b7de63082ffaf5
Source dataset
uspto-grants-2010_06
Patent number
US07727979B2

Reaction notes

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