Triethylamine → N-(1-methyl-piperidin-4-yl)-4-nitro-benzamide

HRID 2111300Notes

Reaction equation

HRID 2111300 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17]>O1CCCC1.O.C(=O)(O)[O-].[Na+]>[CH3:8][N:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:23](=[O:24])[C:22]2[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:27][CH:26]=2)[CH2:3][CH2:4]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 27375314-Amino-1-methylpiperidine

Product 1

HCID 10587627N-(1-methyl-piperidin-4-yl)-4-nitro-benzamideYield 54.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To an ice cooled solution of 3.43 g (0.030 mole) of 4-amino-1-methylpiperidine, 4.58 g (0.045 mole) of triethylamine and 75 mL of tetrahydrofuran, was added a solution of 6.44 g (0.0347 mole) of 4-nitrobenzoyl chloride in 25 mL of tetrahydrofuran. The mixture was stirred at room temperature for 6 hours, then diluted with 50 mL of water and 100 mL of saturated sodium bicarbonate. After stirring another 30 minutes, the mixture was extracted twice with 200 mL of ethyl acetate. The ethyl acetate layers were washed with 200 mL of water, 200 mL of brine, combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 4.34 g of N-(1-methyl-piperidin-4-yl)-4-nitro-benzamide as off-white powder.

Workup

  1. stirringAfter stirring another 30 minutes
  2. extractionthe mixture was extracted twice with 200 mL of ethyl acetate
  3. washThe ethyl acetate layers were washed with 200 mL of water, 200 mL of brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23ce189e1acb43ce9bc6aae48d44453c
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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