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

HRID 2378723Notes

Reaction equation

HRID 2378723 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-62fa03eab4b3426ea160b21197ff76a2
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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