Hydrochloric Acid → HCID 22099427, compound

HRID 1457609Notes

Reaction equation

HRID 1457609 reaction equation
Cl.C(O)C.C(OC([NH:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][N:28]([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32])=[CH:20][CH:19]=1)=O)C1C=CC=CC=1>O.[C].[Pd]>[CH2:33]([N:28]([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:27][CH2:26][CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][NH2:15])=[CH:19][CH:20]=1)[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 22099417HCID 22099417, compound

Product 1

HCID 22099427HCID 22099427, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

Conc. hydrochloric acid (2.1 ml) and g of 10% palladium-carbon (Pd-C) were added to 100 ml of an ethanol solution containing 5.4 g of N-benzyloxycarbonyl-2-[4-(3-dibutylaminopropyloxy)phenyl]ethylamine. The mixture was subjected to catalytic reduction at normal temperature under normal pressure for 1.5 hours. After removing the catalyst by filtration, the filtrate was condensed and the residue was dissolved in water. The aqueous solution was washed with diethyl ether and made alkaline with potassium carbonate, and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure to give 3.2 g of 2-[4-(3-dibutylaminopropyloxy)phenyl]ethylamine (yield: 85%, oily product).

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. customcondensed
  4. washThe aqueous solution was washed with diethyl ether
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed
  7. customdried
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ae898f86d7bf4fa9b12cbcb7abed36a9
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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