HCID 69204801, compound → HCID 69204499, compound

HRID 2117629Notes

Reaction equation

HRID 2117629 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NC1C=CC(N2CCN(CCNC(OC(C)(C)C)=O)CC2)=CC=1>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[CH2:15][CH2:16]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 69204801HCID 69204801, compound

Product 1

HCID 69204499HCID 69204499, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(2-Azidoethyl)-4-(4-nitrophenyl)piperazine (0.8 g, 0.0029 mol) was dissolved in anhydrous ethyl ether (35 mL) under nitrogen, and tributyl phosphine (0.76 mL, 0.0032 mol) was added dropwise. The mixture was stirred at room temperature for 1 h then cooled to −50° C. before adding di-tert-butyldicarbonate (0.63 g, 0.0032 mol dissolved in little ether) and stirring for a further hour. Saturated sodium hydrogen carbonate (2 mL) was added and the flask was allowed to warm to room temperature. Further 20 mL of saturated sodium hydrogen carbonate and 20 mL ethyl acetate were added, the organic phase separated and the aqueous layer extracted with ethyl acetate. The organic layers were combined, dried and evaporated. The crude material was purified on silica (2% MeOH:DCM) to give the title compound. LCMS: 91%, t=1.25 min, [M-56]+=295.32 4-(4-Aminophenyl)-1-(2-tert-butoxycarbonylaminoethyl)piperazine 1-(2-Tert-butoxycarbonylaminoethyl)-4-(4-nitrophenyl)piperazine (0.8 g, 0.0023 mol) was dissolved in ethanol (40 mL) and stirred with Pd/C (10%, 100 mg) under a hydrogen atmosphere overnight. The catalyst was filtered off and solvent evaporated to yield the title compound. LCMS: 90%, t=0.82 min. 1H NMR (CDCl3) 6.85 (2H, d); 6.65 (2H, d); 5.0 (1H, s); 3.3 (2H, t); 3.05 (4H, m); 2.6 (4H, m); 2.5 (2H, t); 1.5 (9H, s).

Workup

  1. filtrationThe catalyst was filtered off
  2. customsolvent evaporated

Sources & evidence

ORD record
ord-c2b30e415cd849e68768417f6b5c2b6a
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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