Triethylamine → Eproxindine

HRID 1381567Notes

Reaction equation

HRID 1381567 reaction equation
[I-].ClC1C=CC=C[N+:4]=1[CH3:9].[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.NCC(O)C[OH:34].[CH2:36]([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH3:37]>C(Cl)Cl.N1C=CC=CC=1>[CH2:36]([N:38]([CH2:41][CH:42]([OH:34])[CH2:9][NH:4][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])[CH2:39][CH3:40])[CH3:37]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 735613-Amino-1,2-propanediolHCID 1670692-Chloro-1-methylpyridinium iodideHCID 131359883-Methoxy-1-phenyl-1H-indole-2-carboxylic acid

Product 1

HCID 54965Eproxindine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

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. After one hour at room temperature, 5.5 g of 3-amino-1,2-propanediol in 50 ml of pyridine are added and the reaction solution is stirred overnight. It is then evaporated, the residue is taken up in methylene chloride and the mixture is washed successively with dilute hydrochloric acid, dilute sodium hydroxide solution and saturated sodium chloride solution. After the organic phase has been dried and evaporated, the oil which remains is taken up in ethyl acetate and recrystallised. Yield: 8.1 g of

Workup

  1. customIt is then evaporated
  2. washthe mixture is washed successively with dilute hydrochloric acid, dilute sodium hydroxide solution and saturated sodium chloride solution
  3. customAfter the organic phase has been dried
  4. customevaporated
  5. customrecrystallised

Sources & evidence

ORD record
ord-3c40a5cebed5492aa866887aec0aa21a
Source dataset
uspto-grants-1989_02
Patent number
US04803198

Reaction notes

Loading…