Triethylamine → Eproxindine

HRID 1650399Notes

Reaction equation

HRID 1650399 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([O:16][CH3:17])=[C:8]2[C:18](Cl)=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:21][CH2:22][CH:23]([OH:30])[CH2:24][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27].C(N(CC)CC)C>C(Cl)Cl>[CH2:26]([N:25]([CH2:24][CH:23]([OH:30])[CH2:22][NH:21][C:18]([C:8]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:15]2[C:10]([C:9]=1[O:16][CH3:17])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:19])[CH2:28][CH3:29])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 977491-Amino-3-(diethylamino)propan-2-olHCID 13135989HCID 13135989, compound

Product 1

HCID 54965Eproxindine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The resulting ethereal solution of N-phenyl-3-methoxyindole-2-carboxylic acid chloride is added dropwise to a solution of 579 g of 1-amino-2-hydroxy-3-diethylaminopropane and 40 g of triethylamine in 70 ml of methylene chloride, whilst cooling with ice. The reaction mixture is stirred at room temperature for 1 hour and then extracted with dilute hydrochloric acid. The hydrochloric acid extract is rendered alkaline by addition of sodium hydroxide solution and is extracted with ether. The ether solution is washed with water, dried over sodium sulphate and evaporated. 110 g of 2-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-methoxy-1-phenylindole remain as an oily base. This base is dissolved in isopropanol and converted into its hydrochloride. Yield: 110 g of the hydrochloride=60.6%, melting point: 148°-150° C.

Workup

  1. temperaturewhilst cooling with ice
  2. extractionextracted with dilute hydrochloric acid
  3. extractionThe hydrochloric acid extract
  4. additionby addition of sodium hydroxide solution
  5. extractionis extracted with ether
  6. washThe ether solution is washed with water
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. dissolutionThis base is dissolved in isopropanol

Sources & evidence

ORD record
ord-3d8a44733dfa4050856d321273cc8f57
Source dataset
uspto-grants-1990_05
Patent number
US04924004

Reaction notes

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