N,N-Dimethyl-1,3-propanediamine → HCID 86667533, compound

HRID 1259010Notes

Reaction equation

HRID 1259010 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][NH2:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][NH:25][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 5049666Sodium triacetoxyborohydrideHCID 5463066HCID 5463066, compound

Product 1

HCID 86667533HCID 86667533, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (9Z,12Z)-octadeca-9,12-dienal (1.06 g, 4.0 mmol) and N,N-dimethylpropane-1,3-diamine (408 mg, 4.0 mmol) in anhydrous tetrahydrofuran (15 mL) was stirred under nitrogen for 15 minutes then sodium triacetoxyborohydride (1.7 g, 8.0 mmol). The solution was stirred for 2 hours at room temperature. Upon completion, the solution was diluted with ethyl acetate (20 mL) and washed with sodium bicarbonate (2×15 mL) and brine (15 mL). The ethyl acetate layer was dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The oil was purified by column chromatography on silica gel (eluted with 100% CH2Cl2 to 1/5/94 NH4OH/MeOH/CH2Cl2) to afford N,N-dimethyl-N′-((9Z,12Z)-octadeca-9,12-dienyl)propane-1,3-diamine as a colorless oil (420 mg, 30%).

Workup

  1. washwashed with sodium bicarbonate (2×15 mL) and brine (15 mL)
  2. dry with materialThe ethyl acetate layer was dried on magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to dryness
  5. customThe oil was purified by column chromatography on silica gel (eluted with 100% CH2Cl2 to 1/5/94 NH4OH/MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-52a980f2cacd46cb8912d8d364255872
Source dataset
uspto-grants-2013_06
Patent number
US08466122B2

Reaction notes

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