Hydrochloric Acid → HCID 20031333, compound

HRID 232307Notes

Reaction equation

HRID 232307 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[CH:5]1([CH:10]=O)[CH2:9][CH2:8][CH2:7][CH2:6]1.C([BH3-])#N.[Na+].Cl>O.CO>[CH2:1]([NH:4][CH2:10][CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7853AllylamineHCID 70106CyclopentanecarbaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 20031333HCID 20031333, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 100 mL of methanol is added 5.7 g (0.1 mol) of 2-propen-1-amine, 9.8 g (0.1 mol) of cyclopentanecarboxaldehyde and 12 g (0.2 mol) of sodium cyanoborohydride. Adjust the pH to 6 with concentrated HCl and monitor the reaction with 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 remove the solvent in vacuo to obtain the title compound.

Workup

  1. customthe reaction with 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. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-55f547dfacba45fca75a1af8c8642fde
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Reaction notes

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