Butylamine → HCID 53709029, compound

HRID 235929Notes

Reaction equation

HRID 235929 reaction equation
[O:1]1[CH2:13][CH:2]1[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[CH2:14]([NH2:18])[CH2:15][CH2:16][CH3:17]>>[CH2:14]([NH:18][CH2:13][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)[CH2:15][CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 8007ButylamineHCID 2736334HCID 2736334, compound

Product 1

HCID 53709029HCID 53709029, compound

Procedure

To 4-(2,3-epoxypropoxy)benzaldehyde (8.9 gms., 0.05 m) is added n-butylamine (30 ml.) and the resulting solution is refluxed 17 hours. The excess n-butylamine is removed under reduced pressure (20 mm). The oil is dissolved in 6N hydrochloric acid (30 ml.) and the solution is heated on a steam bath for 40 minutes. The hot acidic solution is poured into a hot saturated aqueous sodium carbonate solution with nitrogen bubbling through it. The basic solution is extracted with chloroform. The chloroform is dried over sodium sulfate and concentrated to yield 4-(3-n-butylamino-2-hydroxypropoxy)benzaldehyde, as an oil.

Workup

  1. temperaturethe resulting solution is refluxed 17 hours
  2. customThe excess n-butylamine is removed under reduced pressure (20 mm)
  3. dissolutionThe oil is dissolved in 6N hydrochloric acid (30 ml.)
  4. temperaturethe solution is heated on a steam bath for 40 minutes
  5. additionThe hot acidic solution is poured into a hot saturated aqueous sodium carbonate solution with nitrogen bubbling through it
  6. extractionThe basic solution is extracted with chloroform
  7. dry with materialThe chloroform is dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6c4d012b6e334e0abb9af4a9c6210c07
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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