1,3-Propanediamine → HCID 178419944, compound

HRID 434346Notes

Reaction equation

HRID 434346 reaction equation
Cl[C:2](Cl)=[N:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[NH2:17][CH2:18][CH2:19][CH2:20][NH2:21].C(N(CC)CC)C>C(#N)C>[CH:10]1([C:7]2[CH:8]=[CH:9][C:4]([N:3]=[C:2]3[NH:21][CH2:20][CH2:19][CH2:18][NH:17]3)=[CH:5][CH:6]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 4281,3-PropanediamineHCID 8471TriethylamineHCID 20493409HCID 20493409, compound

Product 1

HCID 178419944HCID 178419944, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2.6 g of N-dichloromethylene 4-cyclohexylaniline in 40 ml of acetonitrile is added dropwise to a solution of 1 ml of 1,3-diaminopropane in 20 ml of acetonitrile in 15 minutes at room temperature. After the addition of 1 ml of triethylamine, the solution is stirred for 1 hour at room temperature, after which the reaction mixture is filtered while warm. After distilling off the solvent the residue is taken up in ether and successively washed with 2 N sodium hydroxide solution and water. The ether layer is dried and evaporated, after which the residue is recrystallised from acetonitrile. The resulting 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine has a melting point of 180°-182° C.

Workup

  1. filtrationafter which the reaction mixture is filtered
  2. temperaturewhile warm
  3. distillationAfter distilling off the solvent the residue
  4. washsuccessively washed with 2 N sodium hydroxide solution and water
  5. dry with materialThe ether layer is dried
  6. customevaporated
  7. customafter which the residue is recrystallised from acetonitrile

Sources & evidence

ORD record
ord-66f2affef4a54b20acef455fb374baaf
Source dataset
uspto-grants-1983_08
Patent number
US04396617

Reaction notes

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