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Dimethylformamide → N-[3-(7-methoxyindol-3-yl)-2-propyl]-3-chloromandelamide

HRID 399018
Notes
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Reaction equation

HRID 399018 reaction equation
CN(C=O)C.[NH2:6][CH:7]([CH3:20])[CH2:8][C:9]1[C:17]2[C:12](=[C:13]([O:18][CH3:19])[CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=1)[CH:25]([OH:29])[C:26](O)=[O:27].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(OCC)(=O)C.C(N(CC)CC)C>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH2:8][CH:7]([NH:6][C:26](=[O:27])[CH:25]([C:24]1[CH:30]=[CH:31][CH:32]=[C:22]([Cl:21])[CH:23]=1)[OH:29])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 859813-Chloromandelic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 114242613-(2-Aminopropyl)-7-methoxyindole

Product 1

HCID 18969567N-[3-(7-methoxyindol-3-yl)-2-propyl]-3-chloromandelamideYield 94.1%

Reagents, catalysts & solvents

2
HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a DMF solution (80 ml) containing 3-(2-aminopropyl)-7-methoxyindole (12.24 g) and 3-chloromandelic acid (7.46 g) is added benzotriazole-N-oxytris(dimethylamino)phosphonium hexafluorophosphate (17.68 g), and then thereto is added dropwise triethylamine (9.8 ml). The mixture is stirred at room temperature for five hours, and to the reaction mixture is added ethyl acetate. The mixture is washed successively with water, 10% aqueous citric acid solution, water, a saturated aqueous sodium hydrogen carbonate solution, water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The mixture is evaporated to remove the solvent under reduced pressure, and the residue is purified by silica gel column chromatography (eluent; ethyl acetate/n-hexane=1:1→2:1) to give N-[3-(7-methoxyindol-3-yl)-2-propyl]-3-chloromandelamide (14.02 g) as an oily product.

Workup

  1. washThe mixture is washed successively with water, 10% aqueous citric acid solution, water
  2. dry with materiala saturated aqueous sodium hydrogen carbonate solution, water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  3. customThe mixture is evaporated
  4. customto remove the solvent under reduced pressure
  5. customthe residue is purified by silica gel column chromatography (eluent; ethyl acetate/n-hexane=1:1→2:1)

Sources & evidence

ORD record
ord-dd99aebcf126462dba15c564736a5726
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05817689

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes