Ethylenediamine → N-[3,5-bis(trifluoromethyl)benzyl]ethylenediamine

HRID 1857799Notes

Reaction equation

HRID 1857799 reaction equation
S(Cl)(Cl)=O.ClC1C(C(O)=O)=C(C2C=CC=CC=2)C=CN=1.[CH2:21]([NH2:24])[CH2:22][NH2:23].CS(O[CH2:30][C:31]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:44])([F:43])[F:42])[CH:32]=1)(=O)=O>C1COCC1.CN(C=O)C>[F:38][C:37]([F:39])([F:40])[C:35]1[CH:36]=[C:31]([CH:32]=[C:33]([C:41]([F:44])([F:42])[F:43])[CH:34]=1)[CH2:30][NH:23][CH2:22][CH2:21][NH2:24]

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 24386Thionyl ChlorideHCID 18387265[3,5-Bis(trifluoromethyl)phenyl]methyl methanesulfonateHCID 183873122-Chloro-4-phenylnicotinic acid

Product 1

HCID 18387337N-[3,5-bis(trifluoromethyl)benzyl]ethylenediamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Thionyl chloride (0.15 ml) and DMF (catalytic amount) were added to a THF (5 ml) solution of 2-chloro-4-phenyl-3-pyridinecarboxylic acid (145 mg) and heated under reflux for 2 hours. The solvent was removed by distillation, and the residue was dissolved in THF (5 ml). The resulting solution was added to a mixture of N-[3,5-bis(trifluoromethyl)benzyl]-N'-tert-butoxycarbonylethylenediamine (240 mg), triethylamine (0.26 ml) and THF (10 ml), while cooling with ice, and stirred for 3 hours at room temperature. The N-[3,5-bis(trifluoromethyl)benzyl]-N'-tert-butoxycarbonylethylenediamine used herein was prepared as an oily compound, by reacting ethylenediamine with 3,5-bis(trifluoromethyl)benzyl methanesulfonate in THF to give an oily compound of N-[3,5-bis(trifluoromethyl)benzyl]ethylenediamine, followed by further reacting the compound with di-tert-butyl dicarbonate in the presence of triethylamine in THF.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed by distillation
  4. dissolutionthe residue was dissolved in THF (5 ml)
  5. additionThe resulting solution was added to a mixture of N-[3,5-bis(trifluoromethyl)benzyl]-N'-tert-butoxycarbonylethylenediamine (240 mg), triethylamine (0.26 ml) and THF (10 ml)
  6. temperaturewhile cooling with ice
  7. customwas prepared as an oily compound

Sources & evidence

ORD record
ord-e1f864373e784c9a91a240d1639194f3
Source dataset
uspto-grants-2000_11
Patent number
US06147071

Reaction notes

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