Water → Eproxindine

HRID 1650402Notes

Reaction equation

HRID 1650402 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[C:10]1([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([O:25][CH3:26])=[C:17]2[C:27](O)=[O:28])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:30]([N:32]([CH2:35][CH:36]([OH:39])[CH2:37][NH2:38])[CH2:33][CH3:34])[CH3:31].O>C(Cl)Cl.C(N(CC)CC)C>[CH2:30]([N:32]([CH2:35][CH:36]([OH:39])[CH2:37][NH:38][C:27]([C:17]1[N:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:24]2[C:19]([C:18]=1[O:25][CH3:26])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:28])[CH2:33][CH3:34])[CH3:31]

Participants

7

Reactant 4

HCID 962WaterHCID 977491-Amino-3-(diethylamino)propan-2-olHCID 1670692-Chloro-1-methylpyridinium iodideHCID 131359883-Methoxy-1-phenyl-1H-indole-2-carboxylic acid

Product 1

HCID 54965Eproxindine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

15 g of 2-chloro-N-methyl-pyridinium iodide in 150 ml of methylene chloride and 14 ml of triethylamine are added to 13.3 g of N-phenyl-3-methoxyindole-2-carboxylic acid, dissolved in 100 ml of methylene chloride, and the mixture is stirred at room temperature for one hour. 7.5 g of 3-(N,N-diethylamino)-2-hydroxypropylamine are then added, and the mixture is stirred at room temperature for a further 3 hours. The reaction solution is added to water and the mixture is extracted with methylene chloride. The organic phase is washed with dilute sodium hydroxide solution and water, dried and evaporated. The resulting oily title compound is converted into its hydrochloride in a manner corresponding to that in Example 1. Melting point: 148°-150° C., yield: 12 g.

Workup

  1. stirringthe mixture is stirred at room temperature for a further 3 hours
  2. extractionthe mixture is extracted with methylene chloride
  3. washThe organic phase is washed with dilute sodium hydroxide solution and water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-abecff870c7843f3b27aa4a9029714a3
Source dataset
uspto-grants-1990_05
Patent number
US04924004

Reaction notes

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