Hydrochloric Acid → HCID 69341999, compound

HRID 855227Notes

Reaction equation

HRID 855227 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:12])[CH2:10][NH2:11])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[C:19]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].[BH4-].[Na+].Cl>CO>[C:19]([C:23]1[CH:24]=[CH:25][C:26]([CH2:27][NH:11][CH2:10][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=2)[CH3:12])=[CH:29][CH:30]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 703244-tert-ButylbenzaldehydeHCID 4311764Sodium borohydrideHCID 16219122HCID 16219122, compound

Product 1

HCID 69341999HCID 69341999, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

618 mg of [rac]-2-(4-chloro-phenyl)-propylamine hydrochloride (3 mmol) were dissolved in 8 ml methanol at rt and treated with 415 mg of potassium carbonate (3 mmol) and after 5 min stirring treated with 0.755 ml of 4-tert-butylbenzaldehyde (4.5 mmol). After 30 min stirring at rt, the reaction mixture was refluxed for 3 h, and After cooling down to rt, treated with 170 mg (4.5 mmol) sodium borohydride in portions. After 10 min at rt, the reaction mixture was refluxed for 20 h. After cooling down to rt, the reaction mixture was treated with 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:2) to give 753 mg light brown oil (79%). MS(ISP) 316.3 (M+H)+.

Workup

  1. stirringAfter 30 min stirring at rt
  2. temperaturethe reaction mixture was refluxed for 3 h
  3. temperaturethe reaction mixture was refluxed for 20 h
  4. temperatureAfter cooling down to rt
  5. concentrationconcentrated in vacuo
  6. additionThe residue was diluted with water/EtOAc
  7. customAfter separation of the organic phase
  8. extractionthe aqueous phase was extracted with EtOAc
  9. washthe combined organic phases were washed with brine
  10. dry with materialdried with magnesium sulfate
  11. filtrationfiltered off
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:2)

Sources & evidence

ORD record
ord-765fd01428b24eaf97e2330be03aa38d
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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