1,2-Dichloroethane → Tert-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate

HRID 601027Notes

Reaction equation

HRID 601027 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[N:32]1([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.[OH-].[Na+]>CN(C=O)C>[C:41]([O:40][C:38]([N:32]1[CH2:37][CH2:36][N:35]([C:6](=[O:8])[C:5]2[CH:4]=[CH:3][C:2]([NH2:1])=[CH:10][CH:9]=2)[CH2:34][CH2:33]1)=[O:39])([CH3:44])([CH3:42])[CH3:43]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 2763355Tert-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-aminobenzoic acid (411 mg, 3.00 mmol) in DMF (3.0 mL) at room temperature was added EDC (862 mg, 4.50 mmol), HOBt (608 mg, 4.50 mm01), triethylamine (606 mg, 0.835 mL, 6.00 mmol) and tert-butyl piperazinecarboxylate (671 mg, 3.60 mmol). The mixture was stirred for 22 h, and then 2 N aq. NaOH was added to adjust the PH>10. The mixture was extracted with ethyl acetate, and the organic layer was dried over MgSO4, concentrated. The residue was purified by silica gel column chromatograghy eluted with EtOAc:hexanes (50 to 90% EtOAc) to give 4-(4-amino-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (796 mg, 87%) as a colorless oil. MS (ES+): m/z=306.2

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatograghy
  5. washeluted with EtOAc

Sources & evidence

ORD record
ord-ec90e0f76d94466181e9cebac0f2632c
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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