Hydrochloric Acid → HCID 83660903, compound

HRID 1403122Notes

Reaction equation

HRID 1403122 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+].II.Cl.[OH-].[Na+]>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 83779790HCID 83779790, compound

Product 1

HCID 83660903HCID 83660903, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of ethyl-4-(4-cyanophenyl)-1-piperazine carboxylate (10 g), sodium borohydride (3.4 g), and tetrahydrofuran (50 mL) was added a mixture of iodine (9.8 g) and tetrahydrofuran (50 mL) under a nitrogen gas flow while ice-cooling, followed by stirring at the same temperature for 1 hour, and then further heating and refluxing for 3 hours. The reaction solution was ice-cooled and a 6 M hydrochloric acid solution was added thereto to adjust the pH to 1. The reaction solution was stirred at 70° C. for 30 minutes. After leaving to be cooled, sodium hydroxide was added thereto to adjust the pH to 10, followed by extraction with ethyl acetate. The extracts were washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was made into powder using tetrahydrofuran, ethyl acetate, and diisopropyl ether, to obtain ethyl-4-[4-(aminomethyl)phenyl]-1-piperazine carboxylate (5.2 g).

Workup

  1. additionwas added
  2. temperaturecooling
  3. temperaturefurther heating
  4. temperaturerefluxing for 3 hours
  5. temperaturecooled
  6. stirringThe reaction solution was stirred at 70° C. for 30 minutes
  7. customAfter leaving
  8. temperatureto be cooled
  9. extractionfollowed by extraction with ethyl acetate
  10. washThe extracts were washed with saturated brine
  11. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  12. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-18570bb9e0e2415d838910d6c36e3319
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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