Hydrochloric Acid → 5-(2-Aminoethyl)-2-methoxyphenylamine

HRID 551603Notes

Reaction equation

HRID 551603 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13]C(=O)C)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl>>[NH2:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([NH2:2])[CH:4]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 45074592N-(3-Amino-4-methoxyphenethyl)acetamide hydrochloride

Product 1

HCID 233197675-(2-Aminoethyl)-2-methoxyphenylamineYield 94%

Procedure

N-[-2-(3-amino-4-methoxyphenyl)ethyl]acetamide hydrochloride, prepared as described in Example 8 (15 g) and 175 mL of 2N HCl were heated at reflux for 6 hours. The solvent was removed by rotary evaporation, and the residue was washed with ethanol. The resulting white precipitate was filtered off and dried in vacuum, yielding 13.7 g (94%) of 5-(2-aminoethyl)-2-methoxyphenylamine (AMMPA) dihydrochloride as white crystals. 1HNMR (DMSO-d6) spectrum was consistent with the desired product.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 6 hours
  3. customThe solvent was removed by rotary evaporation
  4. washthe residue was washed with ethanol
  5. filtrationThe resulting white precipitate was filtered off
  6. customdried in vacuum

Sources & evidence

ORD record
ord-2e7c11cc7b2848d7b50355063670ea45
Source dataset
uspto-grants-2011_05
Patent number
US07947761B2

Reaction notes

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