4-Methylmorpholine → 1-tert-Butoxycarbonyl-4-[4-(4-pyridyl)benzoyl]piperazine

HRID 352719Notes

Reaction equation

HRID 352719 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:26]([O:25][C:23]([N:17]1[CH2:22][CH2:21][N:20]([C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:4]=[CH:3][N:2]=[CH:7][CH:6]=3)=[CH:16][CH:15]=2)[CH2:19][CH2:18]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574326074-(Pyridin-4-yl)benzoic acid hydrochloride

Product 1

HCID 227094431-tert-Butoxycarbonyl-4-[4-(4-pyridyl)benzoyl]piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (40 ml), 4-(4-pyridyl)benzoic acid hydrochloride (654 mg) and tert-butyl 1-piperazinecarboxylate (569 mg) were suspended. To the resulting suspension, 1-hydroxybenzotriazole (374 mg) and N-methylmorpholine (336 μl) were added. The resulting mixture was ice cooled, followed by the addition of 1-(3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (796 mg). After stirring at room temperature for 7 hours, the solvent was distilled off. The residue was purified by chromatography on a silica gel column (2% methanol—dichloromethane), followed by washing with hexane, whereby the title compound (905 mg, 89%) was obtained.

Workup

  1. temperaturecooled
  2. distillationthe solvent was distilled off
  3. customThe residue was purified by chromatography on a silica gel column (2% methanol—dichloromethane)
  4. washby washing with hexane, whereby the title compound (905 mg, 89%)
  5. customwas obtained

Sources & evidence

ORD record
ord-b9d70e5f9668448d85d5a0ed3dd1d370
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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