Propionic Acid → HCID 22167639, compound

HRID 1031406Notes

Reaction equation

HRID 1031406 reaction equation
[BH4-].[Na+].[C:3](O)(=O)[CH2:4][CH3:5].[CH3:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[OH-].[Na+]>>[CH3:8][N:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 4

HCID 1032Propionic AcidHCID 14798Sodium HydroxideHCID 75538OctylmethylamineHCID 4311764Sodium borohydride

Product 1

HCID 22167639HCID 22167639, compoundYield 63%

Procedure

Sodium borohydride (6.62 g) was added in portions to propionic acid (52.5 ml), cooled to 5°, maintaining the temperature below 20°. N-methyloctylamine (5 g) was added dropwise, keeping the temperature at 20°. The reaction was stirred at 80° for 3 hours, cooled and basified with 2N sodium hydroxide. The aqueous solution was extracted with dichloromethane (2×75 ml). The combined extracts were dried with anhydrous magnesium sulphate and evaporated to dryness. The resulting oil was purified by column chromatography to give N-methyl-N-propyloctylamine as a colourless oil (4.09 g, 63%).

Workup

  1. temperaturecooled to 5°
  2. temperaturemaintaining the temperature below 20°
  3. customat 20°
  4. temperaturecooled
  5. extractionThe aqueous solution was extracted with dichloromethane (2×75 ml)
  6. dry with materialThe combined extracts were dried with anhydrous magnesium sulphate
  7. customevaporated to dryness
  8. customThe resulting oil was purified by column chromatography

Sources & evidence

ORD record
ord-6630aab21d134a04a23017c0dda2dc38
Source dataset
uspto-grants-1990_09
Patent number
US04954339

Reaction notes

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