1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 23118622, compound

HRID 2075440Notes

Reaction equation

HRID 2075440 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[C:8]([CH:12]=1)[C:9](O)=[O:10].[NH4+].O[N:26]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[CH:3]([C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[C:8]([CH:12]=1)[C:9]([NH2:26])=[O:10])=[O:2]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 23118632HCID 23118632, compound

Product 1

HCID 23118622HCID 23118622, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-dimethoxymethyl-2-(2-morpholinoethoxy)benzoic acid (0.40 g, 1.23 mmol) obtained in Step 4 in DMF (5.00 mL) was added with 1-hydroxybenzotriazole ammonium salt (0.30 g, 1.97 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.35 g, 1.84 mmol), followed by stirring at room temperature for 35 hours. The solvent of the reaction mixture was evaporated under reduced pressure, and the residue was added with hydrochloric acid (3 mol/L, 3.00 mL), followed by stirring at room temperature for 1 hour. The reaction mixture was neutralized with a saturated aqueous sodium hydrogencarbonate solution (50 mL) and was extracted with ethyl acetate (50 mL×3). After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain 5-formyl-2-(2-morpholinoethoxy)benzamide (0.25 g, 73%).

Workup

  1. customThe solvent of the reaction mixture was evaporated under reduced pressure
  2. additionthe residue was added with hydrochloric acid (3 mol/L, 3.00 mL)
  3. stirringby stirring at room temperature for 1 hour
  4. extractionwas extracted with ethyl acetate (50 mL×3)
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-663b3c1b111b47f4a4e43047cccf600c
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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