Hydrochloric Acid → N-methyl-2-amino-alpha-phenylphenethylamine dihydrochloride

HRID 247748Notes

Reaction equation

HRID 247748 reaction equation
[CH3:1][NH:2][CH:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11]C(=O)C(C)(C)C.[ClH:24]>>[ClH:24].[ClH:24].[CH3:1][NH:2][CH:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 10968937N-[2-(2-methylamino-2-phenylethyl)phenyl]-2,2-dimethylpropanamide

Product 1

HCID 12915163N-methyl-2-amino-alpha-phenylphenethylamine dihydrochlorideYield 98%

Conditions

Temperature
100 °C

Procedure

N-[2-(2-methylamino-2-phenylethyl)phenyl]-2,2-dimethylpropanamide (62 g, 0.2 mol) was dissolved in 6N HCl (124 g) and stirred under a nitrogen atmosphere at 100° C. for 24 hours. The warm reaction mixture (about 35°-40° C.) was extracted with toluene (2×100 ml) to effect recovery of trimethylacetic acid. The aqueous phase was dried by azeotropic distillation with toluene (200 ml) using a Dean-Stark phase separator. The product was collected by filtration, slurried in hot 2-propanol (200 ml), refiltered and dried in vacuo (30 mm) at 45° C. for 12 hours to give N-methyl-2-amino-α-phenylphenethylamine dihydrochloride (58.7 g, 0.196 mol) in 98% yield. The product had a melting point of 251°-253° C.

Workup

  1. customThe warm reaction mixture (about 35°-40° C.)
  2. extractionwas extracted with toluene (2×100 ml)
  3. dry with materialThe aqueous phase was dried by azeotropic distillation with toluene (200 ml)
  4. filtrationThe product was collected by filtration
  5. customdried in vacuo (30 mm) at 45° C. for 12 hours

Sources & evidence

ORD record
ord-fb622050f95a4676afd37151dc90bb52
Source dataset
uspto-grants-1987_11
Patent number
US04709093

Reaction notes

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