Tert-butyl 2-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)carbonyl]morpholine-4-carboxylate → N-(3,4-Dichlorophenyl)-4-(morpholin-2-ylcarbonyl)piperazine-1-carboxamide

HRID 603244Notes

Reaction equation

HRID 603244 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([CH:20]3[O:25][CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]3)=[O:19])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]>FC(F)(F)C(O)=O.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([CH:20]3[O:25][CH2:24][CH2:23][NH:22][CH2:21]3)=[O:19])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 1

HCID 57656874Tert-butyl 2-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)carbonyl]morpholine-4-carboxylate

Product 1

HCID 57656890N-(3,4-Dichlorophenyl)-4-(morpholin-2-ylcarbonyl)piperazine-1-carboxamideYield 97.9%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Trifluoroacetic acid/dichloromethane (1:1, 10 ml) was added to tert-butyl 2-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)carbonyl]morpholine-4-carboxylate (900 mg, impure) followed by stirring for 30 min. The solvent was removed under reduced pressure then taken up in 1M. NaOH (aq.) (30 ml) and extracted with ethyl acetate (3×30 ml). The combined organic layers were dried (MgSO4), filtered and evaporated to form the title compound (700 mg) as a white foam which was used without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionNaOH (aq.) (30 ml) and extracted with ethyl acetate (3×30 ml)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9599a525151141fcadf6c5180a3eb868
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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