Hydrochloric Acid → N-[2-Methylamino-2-methylpropyl]benzamide

HRID 2072005Notes

Reaction equation

HRID 2072005 reaction equation
C([CH2:8][NH:9][C:10]([CH3:22])([CH3:21])[CH2:11][NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C1C=CC=CC=1.Cl.C(OCC)(=O)C.Cl.CNC(C)(C)CNC(=O)C1C=CC=CC=1>C(O)(=O)C.CCOCC.[Pd](Cl)Cl>[CH3:8][NH:9][C:10]([CH3:22])([CH3:21])[CH2:11][NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21409888N-[2-benzylmethylamino-2-methylpropyl]benzamideHCID 21409933HCID 21409933, compound

Product 1

HCID 21409819N-[2-Methylamino-2-methylpropyl]benzamideYield 70%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

N-[2-benzylmethylamino-2-methylpropyl]benzamide (3.55 g.,) was dissolved in glacial acetic acid (30 ml.) and hydrogenated over palladium chloride (140 mg.) 320 ml of H2 was taken up. The catalyst was filtered and the filtrate washed with ether (2 × 100 ml.). The filtrate was then made alkaline with 5N sodium hydroxide and extracted with ether (3 × 60 cm3). The ether extracts were dried (anhyd. Na2SO4), filtered and the excess ether evaporated under reduced pressure to give a liquid residue (2.7 g.) the liquid was dissolved in ether (30 ml.). To this was added ethereal HCl in a dropwise manner. The excess ether was evaporated under reduced pressure to give a sticky solid which was refluxed with ethyl acetate for two hours. On cooling crystals of N-[2-methylamino-2-methylpropyl]benzamide hydrochloride were obtained in 70% yield.

Workup

  1. filtrationThe catalyst was filtered
  2. washthe filtrate washed with ether (2 × 100 ml.)
  3. extractionextracted with ether (3 × 60 cm3)
  4. dry with materialThe ether extracts were dried (anhyd. Na2SO4)
  5. filtrationfiltered
  6. customthe excess ether evaporated under reduced pressure
  7. customto give a liquid residue (2.7 g.) the liquid
  8. customThe excess ether was evaporated under reduced pressure
  9. customto give a sticky solid which
  10. customwere obtained in 70% yield

Sources & evidence

ORD record
ord-e85a8d278b81424cac44d3fb04de1c89
Source dataset
uspto-grants-1977_09
Patent number
US04049663

Reaction notes

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