Decanal → HCID 86645269, compound

HRID 1255386Notes

Reaction equation

HRID 1255386 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][NH:11][CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(C)CCN)(OC(C)(C)C)=O.[CH:25](=O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C([BH3-])#N.[Na+]>CO>[C:1]([NH:8][CH2:9][CH2:10][N:11]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH3:12])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 8175DecanalHCID 2756424N-Boc-N-methylethylenediamineHCID 3435744N-(tert-Butoxycarbonyl)-N'-methylethylenediamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 86645269HCID 86645269, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N—BOC—N′-methylethylenediamine and N—BOC—N-methylethylenediamine (1:1, 1.73 g, 4.96 mmol each) in MeOH (50 mL) were added decanal (9.31 g, 59.6 mmol) followed by sodium cyanoborohydride (585 mg, 9.31 mmol) at room temperature. The reaction was stirred overnight at room temperature. The reaction was concentrated on a rotevaporator and the concentrate was diluted with water (50 mL). The pH was lowered to ˜2 with 6 N HCl and the acidic solution was extracted with ethylacetate (3×100 mL). The amine products were extracted into the organic phase. The ethylacetate portion was washed with 0.1 N NaOH (1×100 mL) and brine (2×100 mL) and the solvent was removed. The resulting liquid was dried overnight in vacuo at room temperature. The product was isolated by column chromatography on silica gel column (4×15 cm). Side products were eluted from the column with land 2% MeOH in CH2Cl2 then the product was eluted with 5 and 10% MeOH in CH2Cl2. The solvent was removed from the product fractions and the residue was dried in vacuo at rt to yield N—BOC—N′-decyl-N′-methylethylenediamine as a pale yellow solid (470 mg, 21%): TLC (silica gel, 1 MeOH:9 CH2Cl2) Rf=0.6; 1H NMR (DMSO-d6) δ 0.82 (t, 3H), 1.23 (s, 16H), 1.35 (s, 9H), 2.10 (s, 3H), 2.25 (m, 4H), 2.95 (m, 2H), 6.80 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated on a rotevaporator
  2. additionthe concentrate was diluted with water (50 mL)
  3. extractionthe acidic solution was extracted with ethylacetate (3×100 mL)
  4. extractionThe amine products were extracted into the organic phase
  5. washThe ethylacetate portion was washed with 0.1 N NaOH (1×100 mL) and brine (2×100 mL)
  6. customthe solvent was removed
  7. customThe resulting liquid was dried overnight in vacuo at room temperature
  8. customThe product was isolated by column chromatography on silica gel column (4×15 cm)
  9. washSide products were eluted from the column with land 2% MeOH in CH2Cl2
  10. washthe product was eluted with 5 and 10% MeOH in CH2Cl2
  11. customThe solvent was removed from the product fractions
  12. customthe residue was dried in vacuo at rt

Sources & evidence

ORD record
ord-4c21f162c7594bd9b584ccc0e3e9e813
Source dataset
uspto-grants-2013_06
Patent number
US08460862B2

Reaction notes

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