Hydrochloric Acid → N-(Prop-2-en-1-yl)heptan-1-amine

HRID 232259Notes

Reaction equation

HRID 232259 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[CH:5](=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C([BH3-])#N.[Na+].Cl>O.CO>[CH2:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7853AllylamineHCID 8130HeptanalHCID 5003444Sodium cyanoborohydride

Product 1

HCID 15629611N-(Prop-2-en-1-yl)heptan-1-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 100 mL of methanol is added 2-propenylamine (5.7 g, 0.1 mol), 11.4 g (0.1 mol) of heptaldehyde, and 12 g (0.2 mol) of sodium cyanoborohydride. The pH is adjusted to six with concentrated HCl. Monitor the reaction by thin-layer chromatography. Upon completion, add concentrated HCl until gas evolution ceases. Add 300 mL of H2O and extract once with 200 mL of ether. Add 1N NaOH to the aqueous solution until it is basic and extract twice with 200 mL of ether. Dry the organic phase over Na2SO4. Filter off the drying agent and evaporate the solvent in vacuo to obtain the title compound.

Workup

  1. customMonitor the reaction by thin-layer chromatography
  2. extractionextract once with 200 mL of ether
  3. additionAdd 1N NaOH to the aqueous solution until it
  4. extractionextract twice with 200 mL of ether
  5. dry with materialDry the organic phase over Na2SO4
  6. filtrationFilter off the drying agent
  7. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-c1e36d85dfd74e0eac0b191df81269ad
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Reaction notes

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