Hydrochloric Acid → HCID 68761439, compound

HRID 1615751Notes

Reaction equation

HRID 1615751 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH2:13])[CH2:11][NH2:12])=[CH:6][CH:5]=1.[OH-:14].[Na+].[O:16]1[CH2:22][C:21](=O)[CH2:20][O:19][CH2:18][CH2:17]1.[CH:24](Cl)(Cl)Cl.Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[NH:13][C:24](=[O:14])[C:21]3([CH2:22][O:16][CH2:17][CH2:18][O:19][CH2:20]3)[NH:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 468563761,4-Dioxepan-6-oneHCID 68762575HCID 68762575, compound

Product 1

HCID 68761439HCID 68761439, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

0.68 g (3.0 mmol) 1-(4-fluorophenyl)ethane-1,2-diamine dihydrochloride were placed with 32 mg (0.14 mmol) benzyltriethylammonium chloride in 6 ml dichloromethane and cooled with ice/acetone. Then 1.0 ml (19 mmol) 50% sodium hydroxide solution were added. At 0° C. 0.44 g (3.0 mmol) 80% [1,4]dioxepan-6-one were added dropwise together with 0.37 ml (4.6 mmol) chloroform and 5 ml dichloromethane. The reaction mixture was left overnight to warm up to RT. Then the reaction mixture was acidified with an aqueous 4N hydrochloric acid solution. The phases were separated. The aqueous phase was made alkaline with a 4N sodium hydroxide solution and extracted with ethyl acetate. The combined organic phases were dried and evaporated to dryness by rotary evaporation. Purification was carried out by flash chromatography.

Workup

  1. customAt 0° C
  2. customThe phases were separated
  3. extractionextracted with ethyl acetate
  4. customThe combined organic phases were dried
  5. customevaporated to dryness by rotary evaporation
  6. customPurification

Sources & evidence

ORD record
ord-7892f33ba413406a9a226e8ee9aed2d7
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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