Hydrochloric Acid → N-2-Propen-1-ylcyclohexanemethanamine

HRID 2073730Notes

Reaction equation

HRID 2073730 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[CH:5]1([CH:11]=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[BH3-]C#N.[Na+].Cl>O.CO>[CH2:1]([NH:4][CH2:11][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7853AllylamineHCID 16275CyclohexanecarboxaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 10130064N-2-Propen-1-ylcyclohexanemethanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 100 mL of MeOH is added 2-propenylamine (5.7 g, 0.1 mol), 11.2 g (0.1 mol) of cyclohexane carboxaldehyde and 12 g (0.2 mol) of NaBH3CN. The pH is adjusted to 6 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 Et2O. Add 1N NaOH to the aqueous solution until it is basic (pH=11) and extract 2 times with 200 mL of Et2O. Dry the organic phase over Na2SO4. Filter 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 Et2O
  3. additionAdd 1N NaOH to the aqueous solution until it
  4. extractionextract 2 times with 200 mL of Et2O
  5. dry with materialDry the organic phase over Na2SO4
  6. filtrationFilter the drying agent
  7. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-0a40ab4eb2a24b0e984755751c42acc0
Source dataset
uspto-grants-1990_04
Patent number
US04920116

Reaction notes

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