Heptanal → HCID 86645270, compound

HRID 1255387Notes

Reaction equation

HRID 1255387 reaction equation
[C:1]([NH:8][CH2:9][CH2:10]N)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:12](=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20]([BH3-])#[N:21].[Na+]>CO>[C:1]([NH:8][CH2:9][CH2:10][N:21]([CH2:20][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8130HeptanalHCID 187201N-BOC-ethylenediamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 86645270HCID 86645270, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N—BOC-ethylenediamine (500 mg, 3.12 mmol) in MeOH (15 mL) were added heptanal (802 mg, 7.02 mmol) followed by sodium cyanoborohydride (588 mg, 9.36 mmol) and 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 layer was washed with 0.1 N NaOH (1×100 mL) and brine (2×100 mL) and the solvent was removed. The product was isolated by column chromatography on silica gel. The solvent was removed from the product fractions and the residue was dried in vacuo at room temperature to yield two major products N—BOC—N′,N′-diheptylethylenediamine (0.51 g, 46%): TLC (silica gel, 1 MeOH:9 CH2Cl2) Rf=0.81; and N—BOC—N′-heptylethylenediamine (0.23 g, 15%): TLC (silicagel 9:1 dichloromethane:methanol) Rf=0.66.

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. washThe layer was washed with 0.1 N NaOH (1×100 mL) and brine (2×100 mL)
  5. customthe solvent was removed
  6. customThe product was isolated by column chromatography on silica gel
  7. customThe solvent was removed from the product fractions
  8. customthe residue was dried in vacuo at room temperature

Sources & evidence

ORD record
ord-fbb4fff41a1b4fd190db89807226468e
Source dataset
uspto-grants-2013_06
Patent number
US08460862B2

Reaction notes

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