N-Methylpropylamine → HCID 68814733, compound

HRID 732474Notes

Reaction equation

HRID 732474 reaction equation
[C:1]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=[C:5]([C:7]([O-:9])=O)[CH:4]=[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=1.ON1C2C=CC=CC=2N=N1.Cl.[CH3:31][N:32](C)[CH2:33][CH2:34][CH2:35]N=C=NCC.CNCCC>ClCCl>[CH2:13]([O:12][C:10](=[O:11])[C:3]1[CH:4]=[C:5]([C:7](=[O:9])[N:32]([CH3:31])[CH2:33][CH2:34][CH3:35])[CH:6]=[C:1]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:2]=1)[CH3:14]

Participants

6

Reactant 4

HCID 12315N-MethylpropylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 225750493,5-Bis(ethoxycarbonyl)benzoate

Product 1

HCID 68814733HCID 68814733, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Stir a solution of diethyl 1,3,5-benzene tricarboxylate (2.47 g, 9.28 mmol), 1-hydroxybenzotriazole (1.38 g, 10.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (1.96 g, 10.2 mmol), N-methylpropylamine (1.04 mL, 10.2 mmol) in dichloromethane (50 mL) at room temperature overnight. Dilute with dichloromethane (300 mL) and extract the solution with 0.1 N citric acid (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), and saturated aqueous sodium chloride (50 mL). Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes) to give the title compound (2.02 g, 68%).

Workup

  1. extractionextract the solution with 0.1 N citric acid (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), and saturated aqueous sodium chloride (50 mL)
  2. dry with materialDry (magnesium sulfate)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-445c861d147f49948bc74202b18aa380
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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