Tris(hydroxymethyl)aminomethane → N-(3,4-Dichlorophenyl)piperazine-1-carboxamide

HRID 2371168Notes

Reaction equation

HRID 2371168 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[N:12]1(C(OC(C)(C)C)=O)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(O)C(N)(CO)CO>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 76073,4-Dichlorophenyl isocyanateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 16775732N-(3,4-Dichlorophenyl)piperazine-1-carboxamideYield 109.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3,4-Dichlorophenylisocyanate (3.43 g) and tert-butyl piperazine-1-carboxylate (3.40 g) were stirred for 18 hours in chloroform (20 ml) at room temperature. Trisamine resin (1 g) was added and the mixture stirred for 3 hours, then filtered off. Trifluoroacetic acid (10 ml) was added to the filtrate and this mixture was stirred for two hours. The reaction mixture was concentrated in vacuo and the resulting oil separated between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (100 ml). The ethyl acetate layer was separated, dried over magnesium sulphate, filtered then concentrated in vacuo to give the title compound (5.47 g).

Workup

  1. filtrationfiltered off
  2. additionTrifluoroacetic acid (10 ml) was added to the filtrate
  3. stirringthis mixture was stirred for two hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe resulting oil separated between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (100 ml)
  6. customThe ethyl acetate layer was separated
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-77096a1bd15b4f48839123786ea5cae2
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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