tert-Butyl piperazine-1-carboxylate → HCID 18536079, compound

HRID 412158Notes

Reaction equation

HRID 412158 reaction equation
[Br:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][C:5]([O:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].O.ON1C2C=CC=CC=2N=N1.Cl.CN(CCCN=C=NCC)C>CN(C)C=O.CCOC(C)=O>[Br:1][C:2]1[C:7]([C:8]([N:26]2[CH2:25][CH2:24][N:23]([C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[CH2:28][CH2:27]2)=[O:10])=[CH:6][C:5]([O:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18536005HCID 18536005, compound

Product 1

HCID 18536079HCID 18536079, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution the product from Step A (858 mg, 2.89 mmol), N-tert-butoxycarbonylpiperazine (540 mg, 2.89 mmol), and 1-hydroxybenzotriazole hydrate (546 mg, 4.05 mmol) in 4 mL of dimethylformamide was added 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (718 mg, 3.75 mmol). After 30 minutes, the reaction was poured into EtOAc and washed with water, 3N HCl solution, saturated NaHCO3 solution, and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated as a white foam which was used without further purification.

Workup

  1. washwashed with water, 3N HCl solution, saturated NaHCO3 solution, and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was isolated as a white foam which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-f25c810fff5646e7bd10614a16826562
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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