Hydrochloric Acid → HCID 3249029, compound

HRID 855228Notes

Reaction equation

HRID 855228 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH2:21][CH2:22][NH2:23].[BH4-].[Na+].Cl>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:23][CH2:22][CH2:21][C:15]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[Cl:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 703244-tert-ButylbenzaldehydeHCID 1429382,4-DichlorophenethylamineHCID 4311764Sodium borohydride

Product 1

HCID 3249029HCID 3249029, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.753 ml of 4-tert-butylbenzaldehyde (4.5 mmol) and 0.436 ml of 2-(2,4-dichloro-phenyl)-ethylamine (3 mmol) were dissolved in 8 ml methanol at rt and after 30 min at rt refluxed for 3.5 h. After cooling down to rt, 170 mg (4.5 mmol) of sodium borohydride were added in portions and the reaction mixture was then refluxed overnight. 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 691 mg colorless oil (68%). MS(ISP) 336.3 (M+H)+.

Workup

  1. temperaturerefluxed for 3.5 h
  2. temperaturethe reaction mixture was then refluxed overnight
  3. temperatureAfter cooling down to rt
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with water/EtOAc
  6. customAfter separation of the organic phase
  7. extractionthe aqueous phase was extracted with EtOAc
  8. washthe combined organic phases were washed with brine
  9. dry with materialdried with magnesium sulfate
  10. filtrationfiltered off
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:2)

Sources & evidence

ORD record
ord-dd755bdf8b3e4b0d8a80b3daa442fc18
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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