1-Methylpiperazine → HCID 66906304, compound

HRID 1690626Notes

Reaction equation

HRID 1690626 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][CH:16]=2)=[C:11]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:10]=1)([CH3:8])[CH3:7])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[CH3:62][N:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1>ClCCl>[CH3:29][O:28][CH2:27][CH2:26][CH2:25][O:24][C:11]1[CH:10]=[C:9]([C:6]([CH3:7])([CH3:8])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:30])[CH:14]=[CH:13][C:12]=1[C:15]1[CH:16]=[CH:17][C:18]([C:21]([N:66]2[CH2:67][CH2:68][N:63]([CH3:62])[CH2:64][CH2:65]2)=[O:23])=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 669063764'-(3-Ethoxy-1,1-dimethyl-3-oxopropyl)-2'-(3-methoxypropoxy)biphenyl-4-carboxylic acid

Product 1

HCID 66906304HCID 66906304, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask, under an atmosphere of argon, 4′-(3-ethoxy-1,1-dimethyl-3-oxopropyl)-2′-(3-methoxypropoxy)biphenyl-4-carboxylic acid (1.0 g, 2.4 mmol) was dissolved in dichloromethane (40 mL). EDCl (0.55 g, 2.9 mmol), HOBT (0.39 g, 2.9 mmol) and diisopropylethylamine (2.10 mL, 12.1 mmol) were added at room temperature. After consumption of all the acid, N-methylpiperazine (0.27 mL, 2.4 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, 95/5) to yield 0.51 g (43%) 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, 95/5)

Sources & evidence

ORD record
ord-f18fdec4850f46199dc1d83affa4dba5
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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