1-Piperazinecarboxylic acid, ethyl ester → HCID 10155941, compound

HRID 348077Notes

Reaction equation

HRID 348077 reaction equation
[C:1]([CH2:4][C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)=[O:6])([OH:3])=O.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[CH2:46]([O:48][C:49]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)=[O:50])[CH3:47]>C(Cl)Cl.C(OCC)(=O)C>[CH2:46]([O:48][C:49]([N:51]1[CH2:52][CH2:53][N:54]([C:1]([CH2:4][C:5]([NH:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)=[O:6])=[O:3])[CH2:55][CH2:56]1)=[O:50])[CH3:47]

Participants

8

Reactant 5

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22184909HCID 22184909, compound

Product 1

HCID 10155941HCID 10155941, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-((carboxy)methylcarbonylamino)naphthalene (1.2 g, 5.2 mmol) in CH2Cl2 (40 mL) was added triethylamine (2.2 mL, 15.6 mmol) and 1-hydroxybenzotriazole (HOBT) (0.84 g, 6.2 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI) (1.2 g, 6.2 mmol). After 5 minutes, 1-ethoxycarbonylpiperazine (0.84 mL, 5.3 mmol) was added and the reaction was stirred overnight. The reaction mixture was evaporated in vacuo to afford an oil, which was dissolved in ethyl acetate, and washed with saturated NaHCO3, 1M NaHSO4 and brine. The organic layer was evaporated in vacuo to afford 2-[((4-(ethoxycarbonyl)piperazin-1-yl)carbonylmethyl)carbonyl]aminonaphthalene (1.2 g), as a solid that was used without further purification.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto afford an oil, which
  3. washwashed with saturated NaHCO3, 1M NaHSO4 and brine
  4. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-975a3b77b29b4334b2b7c2ff5c64a9f3
Source dataset
uspto-grants-2007_02
Patent number
US07176207B2

Reaction notes

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