2-benzylamino-N-(1,1-dimethylhexyl)acetamide → A 643C

HRID 1277490Notes

Reaction equation

HRID 1277490 reaction equation
C([NH:8][CH2:9][C:10]([NH:12][C:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:11])C1C=CC=CC=1>C(O)(=O)C.[Pd]>[NH2:8][CH2:9][C:10]([NH:12][C:13]([CH3:19])([CH3:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:11]

Participants

4

Reactant 1

HCID 234541542-benzylamino-N-(1,1-dimethylhexyl)acetamide

Product 1

HCID 128299A 643C

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2-benzylamino-N-(1,1-dimethylhexyl)acetamide (15.8 g, 57 m mol) in acetic acid (160 ml) was hydrogenated over 10% palladium on charcoal (3.16 g) for 2 hours at atmospheric pressure and 80° C. The mixture was filtered and the filtrate evaporated to a viscous liquid (15 g). This was dissolved in water (40 ml), basified with 10 N sodium hydroxide solution and extracted with ether (3×50 ml). The combined extracts were dried over magnesium sulphate then evaporated and distilled to give 2-amino-N-(1,1-dimethylhexyl)acetamide as a colourless oil, b.p. 92°-94° C. at 0.1 mm Hg.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to a viscous liquid (15 g)
  3. dissolutionThis was dissolved in water (40 ml)
  4. extractionextracted with ether (3×50 ml)
  5. dry with materialThe combined extracts were dried over magnesium sulphate
  6. customthen evaporated
  7. distillationdistilled

Sources & evidence

ORD record
ord-0035bbec74254f1cb32c707e02497b53
Source dataset
uspto-grants-1981_07
Patent number
US04277498

Reaction notes

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