Butylamine → HCID 22159590, compound

HRID 855225Notes

Reaction equation

HRID 855225 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].[CH2:13]([NH2:17])[CH2:14][CH2:15][CH3:16].[BH4-].[Na+]>CO.Cl>[CH2:13]([NH:17][CH2:9][C:8]1[CH:11]=[CH:12][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 8007ButylamineHCID 703244-tert-ButylbenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 22159590HCID 22159590, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

0.5 ml of 4-tert-butylbenzaldehyde (3 mmol) and 0.20 ml of butylamine (2 mmol) were dissolved in 5 ml methanol at rt and then refluxed for 17 h. After cooling down to rt, 113 mg (3 mmol) of sodium borohydride were added and the reaction mixture was then refluxed for 3 h. After cooling down to rt, the reaction mixture was treated with 4 drops 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 (8 g silica gel; EtOAc/heptane 1:1) to give 334 mg colorless oil (51%). MS (ISP) 220.4 (M+H)+.

Workup

  1. temperaturerefluxed for 17 h
  2. temperaturethe reaction mixture was then refluxed for 3 h
  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 (8 g silica gel; EtOAc/heptane 1:1)

Sources & evidence

ORD record
ord-c4bf10a6a664481b804f4f6388db5a98
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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