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2,3-Dihydro-α-methyl-N-(phenylmethyl)-1,4-benzodioxin-2-methanamine → 1,4-Benzodioxan, 2-(1-aminoethyl)-

HRID 1855957
Notes
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Reaction equation

HRID 1855957 reaction equation
C([NH:8][CH:9]([CH:11]1[O:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13][CH2:12]1)[CH3:10])C1C=CC=CC=1>CO.Cl.[Pd]>[O:16]1[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13][CH2:12][CH:11]1[CH:9]([NH2:8])[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 5418362,3-Dihydro-α-methyl-N-(phenylmethyl)-1,4-benzodioxin-2-methanamine

Product 1

HCID 171801,4-Benzodioxan, 2-(1-aminoethyl)-Yield 94.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In 50 ml of methanol was dissolved 7 g of pure N-benzyl-1-(1,4-benzodioxan-2-yl)ethylamine (i1 '). After adding one drop of ethanolic hydrochloric acid and 0.5 g of 10% palladium charcoal to the solution, and catalytic reduction was performed at normal pressure until the absorption of hydrogen gas stopped. Then, palladium charcoal was filtered away, the filtrate was acidified with the addition of ethanolic hydrochloric acid, and the solvent was distilled off. Then, 20 ml of isopropanol was added to the residue and the product formed was recovered by filtration to provide 4.4 g (75.7%) of 1-(1,4-benzodioxan-2-yl)ethylamine (i1 ') hydrochloride having a melting point of 234°-235° C. The product was then converted into a base by a conventional manner and distilled under reduced pressure to provide 2.9 g (62.3%) of 1-(1,4-benzodioxan-2-yl)ethylamine (i1 ') having a boiling point of 88°-90° C./0.1 mmHg.

Workup

  1. customwas performed at normal pressure until the absorption of hydrogen gas
  2. filtrationThen, palladium charcoal was filtered away
  3. additionthe filtrate was acidified with the addition of ethanolic hydrochloric acid
  4. distillationthe solvent was distilled off
  5. additionThen, 20 ml of isopropanol was added to the residue
  6. customthe product formed
  7. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-46edf05f45fe46549779640ceeed34e2
Source dataset
uspto-grants-1980_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04217305

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes