1,3-Propanediamine → HCID 21998658, compound

HRID 565227Notes

Reaction equation

HRID 565227 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)#[N:2].[NH2:16][CH2:17][CH2:18][CH2:19][NH2:20]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([NH:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 2

HCID 4281,3-PropanediamineHCID 912824-Oxo-1-phenylcyclohexanenitrile

Product 1

HCID 21998658HCID 21998658, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-cyano-4-phenylcyclohexanone (5.0 g, 25.09 mmol) and 1,3-diaminopropane (5.58 g, 75.3 mmol) and p-toluenesulfonic acid (23 mg) in benzene (50 mL) was refluxed for 4 h in Dean-Stark trap to remove the water that formed. Solvent was evaporated and the residue was redissolved in methanol (40 mL) and cooled to 0° C. To this, sodium borohydride (6.4 5 g) was added in portions and the mixture was stirred at room temperature for 3 h. Solvent was evaporated, the residue was dissolved in dichloromethane (300 mL), washed with brine (3×500 mL), dried (potassium carbonate), and the solvent evaporated to leave the product as a pale yellow viscous oil (4.5 g, 72%). The 1H-NMR showed this product to be pure and found to contain the cis/trans isomers in the ratio of about 4:1.

Workup

  1. temperaturewas refluxed for 4 h in Dean-Stark trap
  2. customto remove the water
  3. customthat formed
  4. customSolvent was evaporated
  5. dissolutionthe residue was redissolved in methanol (40 mL)
  6. additionTo this, sodium borohydride (6.4 5 g) was added in portions
  7. customSolvent was evaporated
  8. dissolutionthe residue was dissolved in dichloromethane (300 mL)
  9. washwashed with brine (3×500 mL)
  10. dry with materialdried (potassium carbonate)
  11. customthe solvent evaporated

Sources & evidence

ORD record
ord-04887c74e64643fda9d7068144e7d2b2
Source dataset
uspto-grants-2001_01
Patent number
US06172066B2

Reaction notes

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