1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21940052, compound

HRID 1242877Notes

Reaction equation

HRID 1242877 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.[CH3:27][N:28]([CH2:30][CH:31]1[CH2:40][CH2:39][C:38]2[C:33](=[CH:34][CH:35]=[C:36](O)[CH:37]=2)[CH2:32]1)[CH3:29].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O.N1C=CC=CC=1>[C:1]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:2]=[CH:3][C:4]([C:7]([O:9][C:36]2[CH:37]=[C:38]3[C:33](=[CH:34][CH:35]=2)[CH2:32][CH:31]([CH2:30][N:28]([CH3:29])[CH3:27])[CH2:40][CH2:39]3)=[O:8])=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 516892Sodium BicarbonateHCID 219397642-(N,N-Dimethylamino)methyl-6-hydroxytetralin

Product 1

HCID 21940052HCID 21940052, compoundYield 53.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Biphenylylcarboxylic acid (580 mg) and WSC (560 mg) were added to pyridine solution (6 ml) of 2-[(N,N-dimethylamino)methyl]-6-hydroxytetralin (300 mg), which was stirred at room temperature for 36 hours. Saturated sodium bicarbonate solution and water were added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using alumina column chromatography (development solvent; hexane˜hexane:ethyl acetate=10:1), and recrystallized (hexane) to give the titled compound (300 mg).

Workup

  1. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified
  5. customrecrystallized (hexane)

Sources & evidence

ORD record
ord-f6c3414d566c4707a7522245e8a83328
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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