Acetic Acid → HCID 22007072, compound

HRID 323715Notes

Reaction equation

HRID 323715 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11](=O)[CH2:12][CH2:13][CH3:14])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH2:16]([NH2:20])[CH2:17][CH2:18][CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[OH-].[Na+]>ClCCCl.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]([NH:20][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8007ButylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 14918192HCID 14918192, compound

Product 1

HCID 22007072HCID 22007072, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

A mixture of 2.0 g (9.7 mmol) of 1-(1,3-benzdioxol-5-yl)pentan-2-one, 0.71 g (9.7 mmol) of n-butylamine, 2.88 g (13.6 mmol) of sodium triacetoxyborohydride and 0.58 g (9.7 mmol) of acetic acid were stirred in 1,2-dichloroethane (34 ml) under argon gas for four days at room temperature. Thereafter, the mixture was alkalized with 1 N sodium hydroxide. Water (50 ml) was added to the mixture and was extracted three times with ether (70 ml). The obtained organic phase was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate, concentrated and purified by column chromatography. Chloroform was used for eluting solvent. 1-(1,3-Benzodioxol-5-yl)-2-butylaminopentane was obtained as light yellow oil.

Workup

  1. extractionwas extracted three times with ether (70 ml)
  2. washThe obtained organic phase was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified by column chromatography
  6. washfor eluting solvent

Sources & evidence

ORD record
ord-a76233316fbd44748c1dd375a5391202
Source dataset
uspto-grants-2001_04
Patent number
US06214859B1

Reaction notes

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