Dimethylamine → HCID 10777845, compound

HRID 1493069Notes

Reaction equation

HRID 1493069 reaction equation
[CH3:1][C:2]1([CH2:14][C:15]([OH:17])=O)[CH2:6][C:5]2[C:7]([CH3:13])=[CH:8][C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1.O.ON1C2C=CC=CC=2N=N1.Cl.[CH2:30]([N:32]=[C:33]=NCCCN(C)C)C.CNC>CN(C)C=O.O>[CH3:30][N:32]([CH3:33])[C:15](=[O:17])[CH2:14][C:2]1([CH3:1])[CH2:6][C:5]2[C:7]([CH3:13])=[CH:8][C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10513860HCID 10513860, compound

Product 1

HCID 10777845HCID 10777845, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4,6,7-tetramethyl-2,3-dihydrobenzofuran-2-yl acetic acid (3.0 g, 12.8 mmol) in dimethylformamide (30 ml) were added 1-hydroxy-1H-benzotriazole monohydrate (HOBt) (2.1 g, 14.1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (WSC) (3.7 g, 19.2 mmol). The mixture was stirred at room temperature for 1 hour. Then, 50% dimethylamine aqueous solution (3 ml) was added and the resulting mixture was stirred for additional 30 minutes. The reaction mixture was diluted with water and the product was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (isopropyl ether) to obtain the desired compound (3.1 g, yield: 92.6% yield) as oil.

Workup

  1. stirringthe resulting mixture was stirred for additional 30 minutes
  2. extractionthe product was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (isopropyl ether)

Sources & evidence

ORD record
ord-20917ba55dc24e7e8633e5aa2c6d092e
Source dataset
uspto-grants-1994_12
Patent number
US05376681

Reaction notes

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