tert-Butyl piperazine-1-carboxylate → HCID 58864146, compound

HRID 1353439Notes

Reaction equation

HRID 1353439 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13](Cl)[C:12]2[C:7](=[CH:8][C:9]([Cl:16])=[CH:10][CH:11]=2)[N:6]=1)=[O:4].[C:17]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>C(N(C(C)C)CC)(C)C>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([N:27]2[CH2:26][CH2:25][N:24]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:29][CH2:28]2)[C:12]2[C:7](=[CH:8][C:9]([Cl:16])=[CH:10][CH:11]=2)[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 29923275Methyl 4,7-dichloroquinoline-2-carboxylate

Product 1

HCID 58864146HCID 58864146, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

The mixture of 4,7-dichloro-2-quinolinecarboxylic acid methyl ester (90.2 g, 379 mmol) and N-boc-piperazine (60.1 g, 387 mmol) in dry diisopropylethyl amine (300 mL) was kept at 140 degrees C. for 3 h. After the removal of diisopropylethyl amine in vacuo, ethyl ether was added to precipitate the product. The crude solid was collected by filtration and was purified by re-crystallization from EtOAc (500 mL) to afford 123 g (80%) of 7-chloro-4-[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]-2-quinolinecarboxylic acid methyl ester as an off-white solid. 1H NMR (DMSO-d6): δ 1.42 (s, 18H), 3.18 (m, 4H), 3.61 (m, 4H), 3.92 (s, 3H), 7.47 (s, 1H), 7.63 (d, 1H), 8.04 (d, 1H), 8.1 (s, 1H).

Workup

  1. customwas kept at 140 degrees C
  2. customAfter the removal of diisopropylethyl amine in vacuo, ethyl ether
  3. additionwas added
  4. customto precipitate the product
  5. filtrationThe crude solid was collected by filtration
  6. customwas purified by re-crystallization from EtOAc (500 mL)

Sources & evidence

ORD record
ord-b4372eda4e9c42f79054715eeb87912d
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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