Tripropylamine → HCID 44213422, compound

HRID 1003728Notes

Reaction equation

HRID 1003728 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]1[N:11]([CH3:12])[C:10](=[O:13])[N:9]([CH3:14])[C:8](=[O:15])[C:7]=1[CH2:16][CH2:17][C:18]#[N:19].[CH2:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH3:21].C(N(CCC)CCC)CC>C1(C)C(C)=CC=CC=1>[C:18]([CH2:17][CH2:16][C:7]1[C:8](=[O:15])[N:9]([CH3:14])[C:10](=[O:13])[N:11]([CH3:12])[C:6]=1[NH:5][CH2:4][CH2:3][CH2:2][N:32]1[CH2:31][CH2:30][N:29]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][CH2:20][CH3:21])[CH2:34][CH2:33]1)#[N:19]

Participants

5

Reactant 3

HCID 7616TripropylamineHCID 833571-(2-Ethoxyphenyl)piperazineHCID 70192625HCID 70192625, compound

Product 1

HCID 44213422HCID 44213422, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4.3 g (15 mmol) of 6-(3-chloropropylamino)-5-cyanoethyl-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione and 4.2 g (15 mmol) of 1-(2-ethoxyphenyl)piperazine are heated at 140° C. for 14 h with 11.4 ml (60 mmol) of tripropylamine in 50 ml of xylene. The reaction mixture is concentrated in vacuo, the residue is taken up with 50 ml of water and 200 ml of ethyl acetate, and the mixture is treated with 300 ml of 1N NaOH, extracted and separated. The organic extract is washed with saturated NaCl solution and dried and the oil obtained after removing the solvent is purified by column chromatography (neutral silica gel, eluent initially ethyl acetate/petroleum ether 1:1, later only petroleum ether). The title compound of m.p. 133-136° C. (from ether) is obtained from the product fractions in a yield of 57%.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionthe mixture is treated with 300 ml of 1N NaOH
  3. extractionextracted
  4. customseparated
  5. extractionThe organic extract
  6. washis washed with saturated NaCl solution
  7. customdried
  8. customthe oil obtained
  9. customafter removing the solvent
  10. customis purified by column chromatography (neutral silica gel, eluent initially ethyl acetate/petroleum ether 1:1, later only petroleum ether)

Sources & evidence

ORD record
ord-21e9c69855a5417592bfa45bc8eae6da
Source dataset
uspto-grants-2000_04
Patent number
US06046329

Reaction notes

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