4-(1,3-Benzodioxol-5-yl)-2-butanone → N-[4-(3,4-methylenedioxyphenyl)-but-2-yl]-beta-(3,4-dihydroxyphenyl) ethylamine hydrochloride

HRID 1580163Notes

Reaction equation

HRID 1580163 reaction equation
C(=O)(O)[O-].[Na+].[ClH:6].[NH2:7][CH2:8][CH2:9][C:10]1[CH:17]=[CH:16][C:14]([OH:15])=[C:12]([OH:13])[CH:11]=1.[CH2:18]1[O:26][C:25]2[CH:24]=[CH:23][C:22]([CH2:27][CH2:28][C:29](=O)[CH3:30])=[CH:21][C:20]=2[O:19]1>[Pt]=O.C(O)C>[ClH:6].[CH2:18]1[O:26][C:25]2[CH:24]=[CH:23][C:22]([CH2:27][CH2:28][CH:29]([NH:7][CH2:8][CH2:9][C:10]3[CH:17]=[CH:16][C:14]([OH:15])=[C:12]([OH:13])[CH:11]=3)[CH3:30])=[CH:21][C:20]=2[O:19]1

Participants

6

Reactant 3

HCID 620984-(1,3-Benzodioxol-5-yl)-2-butanoneHCID 65340Dopamine HydrochlorideHCID 516892Sodium Bicarbonate2×

Product 1

HCID 21565198N-[4-(3,4-methylenedioxyphenyl)-but-2-yl]-beta-(3,4-dihydroxyphenyl) ethylamine hydrochloride

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

In 10 ml. of a saturated solution of sodium bicarbonate is dissolved 1.0 g. (0.00526 mole) dopamine hydrochloride. A solution of 4-[3,4-(methylenedioxy) phenyl]butan-2-one (1.10 g., 0.00526 mole) in 10 ml. ethanol is added to the above sodium bicarbonate solution. A white precipitate develops. The slurry is charged with 0.1 g. platinum oxide and hydrogenated for three hours at 20 psi. The solids are filtered and the solution concentrated. The residue is triturated with ethanol, refiltered and again concentrated. The oily residue is treated with ethereal hydrochloric acid and the so-formed solids collected and crystallized from methanol-isopropanol to give N-[4-(3,4-methylenedioxyphenyl)-but-2-yl]-β-(3,4-dihydroxyphenyl) ethylamine hydrochloride as a white solid, m.p. 204°-206°.

Workup

  1. additionThe slurry is charged with 0.1 g
  2. filtrationThe solids are filtered
  3. concentrationthe solution concentrated
  4. customThe residue is triturated with ethanol
  5. concentrationagain concentrated
  6. additionThe oily residue is treated with ethereal hydrochloric acid
  7. customthe so-formed solids collected
  8. customcrystallized from methanol-isopropanol

Sources & evidence

ORD record
ord-52793458e5874635a19afccfb170c1c9
Source dataset
uspto-grants-1976_01
Patent number
US03932461

Reaction notes

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