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

HRID 982945Notes

Reaction equation

HRID 982945 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, 1 M 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, 1 M NaHSO4 and brine
  4. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-1961de3c129c4540a0f1a043395bb442
Source dataset
uspto-grants-2005_03
Patent number
US06861424B2

Reaction notes

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