Hydrochloric Acid → (R)-1-(3,4-methylenedioxyphenyl)-2-propylaminopentane hydrochloride

HRID 1925489Notes

Reaction equation

HRID 1925489 reaction equation
[ClH:1].[CH2:2]1[O:10][C:9]2[CH:8]=[CH:7][C:6]([CH2:11][C@H:12]([NH:16][CH2:17][CH2:18][CH3:19])[CH2:13][CH2:14][CH3:15])=[CH:5][C:4]=2[O:3]1>C(OCC)C>[ClH:1].[CH2:2]1[O:10][C:9]2[CH:8]=[CH:7][C:6]([CH2:11][C@H:12]([NH:16][CH2:17][CH2:18][CH3:19])[CH2:13][CH2:14][CH3:15])=[CH:5][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67425442(R)-1-(3,4-methylenedioxyphenyl)-2-propylaminopentane

Product 1

HCID 67425441(R)-1-(3,4-methylenedioxyphenyl)-2-propylaminopentane hydrochlorideYield 24%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Saturated hydrogen chloride in diethyl ether (15 mL) was added to a solution of (R)-1-(3,4-methylenedioxyphenyl)-2-propylaminopentane (8.00 g) in diethyl ether (80 mL) under ice-cooling and stirring. The precipitated crystals were collected by filtration and washed four times with diethyl ether (1 mL). The resulting powder (7.44 g) was dissolved by heating in acetone (150 mL), and the solution was concentrated to about 100 mL. The solution was allowed to stand at 5° C. for 15 hours. The precipitated crystals were collected by filtration and washed three times with acetone (5 mL) to give (R)-1-(3,4-methylenedioxyphenyl)-2-propylaminopentane hydrochloride (4.58 g, 24% yield).

Workup

  1. temperaturecooling
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed four times with diethyl ether (1 mL)
  4. dissolutionThe resulting powder (7.44 g) was dissolved
  5. temperatureby heating in acetone (150 mL)
  6. concentrationthe solution was concentrated to about 100 mL
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed three times with acetone (5 mL)

Sources & evidence

ORD record
ord-e25eb5b3bbff4105b70508ce315e46c5
Source dataset
uspto-grants-2012_05
Patent number
US08178686B2

Reaction notes

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