Formaldehyde → HCID 20079836, compound

HRID 1654235Notes

Reaction equation

HRID 1654235 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[C:3]#[C:4][C:5]#[C:6][CH2:7][N:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH2:10][NH2:11].C=O.[C:21]([BH3-])#N.[Na+]>C(O)C>[CH3:21][NH:11][CH2:10][CH2:9][N:8]([CH2:7][C:6]#[C:5][C:4]#[C:3][C:2]([CH3:17])([CH3:18])[CH3:1])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 20079882HCID 20079882, compound

Product 1

HCID 20079836HCID 20079836, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 1 ml of ethanol was dissolved 30 mg of N-(6,6-dimethyl-2,4-heptadiynyl)-N-pentylethylenediamine. Then 20 μl of 35% formalin and 8.3 mg of sodium cyanoborohydride were added to the solution. The mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was fractionated, washed with saturated sodium bicarbonate aqueous solution and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the solvent was then removed under reduced pressure. The residue was purified by silica gel column chromatography (Wako Gel C-200, 10 g, methylene chloride/methanol=50/1) to give 10 mg (yield: 32%) of the title compound as colorless oil.

Workup

  1. extractionThe reaction mixture was extracted with a mixture of ethyl acetate and 1N hydrochloric acid
  2. washwashed with saturated sodium bicarbonate aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe solvent was then removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Wako Gel C-200, 10 g, methylene chloride/methanol=50/1)

Sources & evidence

ORD record
ord-d13f12fdda824e6db7fb471a531e88db
Source dataset
uspto-grants-1995_04
Patent number
US05405873

Reaction notes

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