Hydrochloric Acid → HCID 67017887, compound

HRID 2243173Notes

Reaction equation

HRID 2243173 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH:11][C:12]([C:14]2[S:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[CH:15]=2)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[OH-].[Na+]>C1COCC1>[S:18]1[C:14]([CH2:12][NH:11][CH2:10][CH2:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)=[CH:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67017630HCID 67017630, compound

Product 1

HCID 67017887HCID 67017887, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 364 mg (1.04 mmol) of benzo[b]thiophene-2-carboxylic acid[2-(3,4-di-chloro-phenyl)-ethyl]-amide in 10 ml of THF was added dropwise to 5.2 ml of a 1 molar solution of BH3-THF complex in THF at 0° C. The reaction mixture was stirred for 30 min at RT and then heated to reflux over night. Then 2 ml of 6 N HCl were added very carefully at ambient temperature and the mixture was heated again to reflux for 2 hours. After cooling to RT, the pH was adjusted to 8-9 by addition of 1 N sodium hydroxide solution and the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried with magnesium sulfate, filtered and concentrated. Final purification of the residue (silica gel; dichloromethane/methanol 95:5) yielded 113 mg (32%) of benzo[b]thiophen-2-ylmethyl-[2-(3,4-dichloro-phenyl)-ethyl]-amine as off-white solid. MS (ISP) 336.2 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux over night
  3. temperaturethe mixture was heated again
  4. temperatureto reflux for 2 hours
  5. temperatureAfter cooling to RT
  6. extractionthe mixture was extracted twice with ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customFinal purification of the residue (silica gel; dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-18c17f5ecbfc4437a13cf8bfe74a6d25
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

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