4-Methylmorpholine → 2-Amino-5-(4-methyl-piperazin-1-ylmethyl)benzamide

HRID 591815Notes

Reaction equation

HRID 591815 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:7][C:3]=1[C:4](O)=[O:5].CC[N:21]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[NH4+].[OH-]>C1COCC1.CN(C=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:7][C:3]=1[C:4]([NH2:21])=[O:5]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 666711232-Amino-5-(4-methyl-piperazin-1-ylmethyl)benzoic acid

Product 1

HCID 666710512-Amino-5-(4-methyl-piperazin-1-ylmethyl)benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-amino-5-(4-methyl-piperazin-1-ylmethyl)benzoic acid (crude 1.28 g, 3.00 mmol) in THF (18 mL) and DMF (7 mL), EDCl (0.77 g, 4.00 mmol), and HOBT (0.50 g, 3.30 mmol) were added and stirred at room temperature for 20 minutes. Then, N-methylmorpholine (0.33 g, 3.30 mmol) and NH4OH (aq. 50% v/v, 3.50 mL, 50.0 mmol) were added. The mixture was stirred at room temperature for 48 hours. The solvent was evaporated, the residue was purified by column chromatography (silica gel 230-400 mesh; 5-10% 2 M ammonia in methanol and dichloromethane as eluent) to give 2-amino-5-(4-methyl-piperazin-1-ylmethyl)benzamide as a white solid. Yield: 0.416 g (55% for two steps).

Workup

  1. stirringThe mixture was stirred at room temperature for 48 hours
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography (silica gel 230-400 mesh; 5-10% 2 M ammonia in methanol and dichloromethane as eluent)

Sources & evidence

ORD record
ord-263e1ef7b91c4acc9216eaf2e27469ad
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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