1-Methylpiperazine → Ethyl 3-{2-(3-methoxypropoxy)-4'-[(4-methylpiperazin-1-yl)carbonyl]biphenyl-4-yl}propanoate

HRID 1690617Notes

Reaction equation

HRID 1690617 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=O)=[CH:15][CH:14]=2)=[C:9]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH:8]=1)[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[CH3:60][N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1>ClCCl>[CH3:27][O:26][CH2:25][CH2:24][CH2:23][O:22][C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:28])[CH:12]=[CH:11][C:10]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:64]2[CH2:65][CH2:66][N:61]([CH3:60])[CH2:62][CH2:63]2)=[O:21])=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 669064994'-(3-Ethoxy-3-oxopropyl)-2'-(3-methoxypropoxy)biphenyl-4-carboxylic acid

Product 1

HCID 66906577Ethyl 3-{2-(3-methoxypropoxy)-4'-[(4-methylpiperazin-1-yl)carbonyl]biphenyl-4-yl}propanoateYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask, under an atmosphere of argon, 4′-(3-ethoxy-3-oxopropyl)-2′-(3-methoxypropoxy)biphenyl-4-carboxylic acid (0.48 g, 1.2 mmol) was dissolved in dichloromethane (20 mL). EDCl (0.29 g, 1.5 mmol), HOBT (0.20 g, 1.5 mmol) and diisopropylethylamine (1.08 mL, 6.2 mmol) were added at room temperature. After consumption of all the acid, N-methylpiperazine (0.11 mL, 1.0 mmol) was added and the mixture, was stirred for 18 hrs. The organic layer was washed twice with water. The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/ethanol, 90/10) to yield 0.36 g (62%) of the desired product as a yellow oil.

Workup

  1. additionwas added
  2. washThe organic layer was washed twice with water
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (dichloromethane/ethanol, 90/10)

Sources & evidence

ORD record
ord-5f630f7ac32445a2b201de76aa8c62fa
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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