Diisopropylethylamine → Methyl 2-[(4-tert-Butylpiperazin-1-ylcarbonyl)amino]benzoate

HRID 1247129Notes

Reaction equation

HRID 1247129 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[C:2]=[O:3].Br.Br.[C:16]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([CH3:19])([CH3:18])[CH3:17].C(N(CC)C(C)C)(C)C>ClCCl.CN(C)C=O.C(OCC)(=O)C>[C:16]([N:20]1[CH2:25][CH2:24][N:23]([C:2]([NH:1][C:4]2[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])=[O:3])[CH2:22][CH2:21]1)([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 519494Methyl 2-isocyanatobenzoateHCID 219063541-Tert-butylpiperazine dihydrobromide

Product 1

HCID 21906314Methyl 2-[(4-tert-Butylpiperazin-1-ylcarbonyl)amino]benzoateYield 95.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice cold solution of methyl 2-isocyanatobenzoate (0.18 g, 1.0 mmol) in dichloromethane (3 mL) was added dropwise a solution of 1-tert-butylpiperazine dihydrobromid (0.28 g, 0.92 mmol) and N,N-diisopropylethylamine (0.36 mL, 2.1 mmol) in N,N-dimethylformamide (5 mL). The reaction solution was stirred at room temperature for 1 h, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo to give 0.28 g (95%) of a yellow oil.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-005c2219959546f5864413055cb958a7
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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