Pyridine → HCID 20570857, compound

HRID 1577517Notes

Reaction equation

HRID 1577517 reaction equation
[OH:1][CH:2]([CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:19][CH2:18]1)[CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][N:9]2[CH:14]=[O:15].[C:32](OC(=O)C)(=[O:34])[CH3:33].N1C=CC=CC=1.C[O-].[Na+]>CO>[OH:1][CH:2]([CH2:16][N:17]1[CH2:18][CH2:19][CH:20]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[CH:27][CH:26]=2)[CH2:21][CH2:22]1)[CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][N:9]2[CH:14]=[O:15]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10942334Sodium MethoxideHCID 20570881HCID 20570881, compound

Product 1

HCID 20570857HCID 20570857, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.3 g. 4-{2-Hydroxy-3-[4-(4-aminophenoxymethyl)-piperidino]-propoxy}-1-formylindoline (preparation see Example 15b) are stirred with a mixture of 25 ml. acetic anhydride and 25 ml. pyridine for 10 hours at ambient temperature, then evaporated in a vacuum and the residue dissolved in water and dichloromethane. After neutralization with sodium bicarbonate, the organic phase is distilled and the residue obtained is converted in methanol with sodium methylate solution into the desired compound. By shaking out between dichloromethane and water and evaporating the organic phase, there is obtained 1.0 g. (27% of theory) 4-{2-hydroxy-3-[4-(4-acetamidophenoxymethyl)-piperidino]-propoxy}-1-formylindoline; m.p. 177°-179° C.

Workup

  1. customevaporated in a vacuum
  2. dissolutionthe residue dissolved in water
  3. distillationAfter neutralization with sodium bicarbonate, the organic phase is distilled
  4. customthe residue obtained

Sources & evidence

ORD record
ord-5173f67f0b14442a84175f09aa347c30
Source dataset
uspto-grants-1981_09
Patent number
US04288442

Reaction notes

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