Hydrochloric Acid → Eproxindine

HRID 1650403Notes

Reaction equation

HRID 1650403 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](O)=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(OCC)=O.[CH2:27]([N:29]([CH2:32][CH:33]([OH:36])[CH2:34][NH2:35])[CH2:30][CH3:31])[CH3:28].Cl>C(Cl)Cl.O.C(N(CC)CC)C>[CH2:27]([N:29]([CH2:32][CH:33]([OH:36])[CH2:34][NH:35][C:18]([C:8]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15]2[C:10]([C:9]=1[O:16][CH3:17])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:19])[CH2:30][CH3:31])[CH3:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 977491-Amino-3-(diethylamino)propan-2-olHCID 131359883-Methoxy-1-phenyl-1H-indole-2-carboxylic acid

Product 1

HCID 54965Eproxindine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

6.6 g of N-phenyl-3-methoxyindole-2-carboxylic acid and 7 ml of triethylamine in 75 ml of methylene chloride are added dropwise to 7 g of ethyl chloroformate in 25 ml of methylene chloride at -30° C. The temperature is allowed to rise slowly to 5° C., whilst stirring, and 3.7 g of 3-(N,N-diethylamino)-2-hydroxypropylamine are added. The reaction solution is subsequently stirred at room temperature, poured into water and worked up as described in Example 8. Yield: 4.5 of the hydrochloride of the title compound, melting point: 148°-150° C.

Workup

  1. customto rise slowly to 5° C.
  2. stirringThe reaction solution is subsequently stirred at room temperature

Sources & evidence

ORD record
ord-b0fc1aa683bf4385be183451335e8bab
Source dataset
uspto-grants-1990_05
Patent number
US04924004

Reaction notes

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