Methanol → HCID 21409848, compound

HRID 1283559Notes

Reaction equation

HRID 1283559 reaction equation
C(O[C:4](=[O:6])C)=O.[CH3:7][C:8]([N:15]([CH3:17])[CH3:16])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][NH2:10].[OH-].[Na+].CO>CCOCC>[CH3:7][C:8]([N:15]([CH3:16])[CH3:17])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][NH:10][CH:4]=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 75269Acetic-formic anhydrideHCID 53989671HCID 53989671, compound

Product 1

HCID 21409848HCID 21409848, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of acetic formic anhydride (2.9 mls., 20 mmole) (prepared by stirring acetic anhydride [2.04 ml.] and formic acid [0.86 ml.] on a water bath at 50°-60° for two hrs. and cooling), was added dropwise, with stirring, 2-methyl-2-dimethylamino-hexylamine (2.37 g.,) at such a rate that the temperature never rose above 40°C. The solution was stirred for 30 mins. ether (6 ml) was added, and stirring continued at room temperature overnight. The mixture was diluted with ether (50 ml.), basified with 2N sodium hydroxide solution and extracted with ether (4 × 100 ml.). Evaporation of the washed (2 × 100 ml.), dried (Na2SO4) extracts gave a colourless oil (2.2 g.). T.L.C. (silica, methanol) showed two spots: RF 0.5 and RF 0.0. The oil was chromatographed on a column of silica (20 × 3.0 cm.) eluting with methanol and fractions (6 × 100 ml.) were collected. Fractions 2-5 were combined and evaporated affording N-[2-methyl-2-dimethylamino-hexyl]formamide as a colourless oil (1.427 g., 51%).

Workup

  1. customthat the temperature never rose above 40°C
  2. stirringThe solution was stirred for 30 mins
  3. stirringstirring
  4. extractionextracted with ether (4 × 100 ml.)
  5. customEvaporation of the
  6. washwashed (2 × 100 ml.)
  7. dry with materialdried (Na2SO4)
  8. customextracts gave a colourless oil (2.2 g.)
  9. customThe oil was chromatographed on a column of silica (20 × 3.0 cm.)
  10. washeluting with methanol and fractions (6 × 100 ml.)
  11. customwere collected
  12. customevaporated

Sources & evidence

ORD record
ord-a0988b5bf39f4b75be8ae69d2381a49b
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

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