Triethylamine → 1,4-Bis(phenylmethyl)-N-methoxy-N-methyl-2-piperazine carboxamide

HRID 1713492Notes

Reaction equation

HRID 1713492 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14]C3C=CC=CC=3)[CH2:10][CH:9]2[C:21]([OH:23])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(N=C=NCCCN(C)C)C.ON1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2N=N1.Cl.[CH3:47][NH:48][O:49][CH3:50].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:10][CH:9]2[C:21]([N:48]([O:49][CH3:50])[CH3:47])=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 223242451,4-Dibenzylpiperazine-2-carboxylic acid

Product 1

HCID 231219081,4-Bis(phenylmethyl)-N-methoxy-N-methyl-2-piperazine carboxamideYield 88.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,4-Bis(phenylmethyl)-2-piperazine carboxylic acid (5.0 g, 16 mmol) was dissolved in N,N-dimethylformamide (80 mL). 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.1 g, 16 mmol), 1-hydroxybenzotriazole (2.2 g, 16 mmol), N,O-dimethylhydroxylamine hydrochloride (1.9 g, 19 mmol) and triethylamine (2.7 mL, 19 mmol) were added thereto, and the mixture was stirred at room temperature for 3 days. To the reaction solution was added ethyl acetate, and the resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1) to obtain the title compound (5.0 g, yield 87%).

Workup

  1. washthe resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record
ord-d5864a06f656419285b06e9065f3a3cf
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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