Ethanol → HCID 13019528, compound

HRID 1702592Notes

Reaction equation

HRID 1702592 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=2[C:22]([O:24]C)=[O:23])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[OH-].[Na+].Cl.C(NC1CCN(CCCOC2C=CC=CC=2C(O)=O)CC1)(=O)C1C=CC=CC=1>CC(C)=O>[C:1]([NH:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=2[C:22]([OH:24])=[O:23])[CH2:14][CH2:15]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13019513HCID 13019513, compoundHCID 70544040HCID 70544040, compound

Product 1

HCID 13019528HCID 13019528, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 23.6 g. (0.06 mol) methyl 2-[3-(4-benzamidopiperidino)-propoxy]-benzoate (see Example 2a), 200 ml. ethanol and 200 ml. 1 N aqueous sodium hydroxide solution is heated under reflux for 1 hour, then evaporated and the evaporation residue dissolved in water and acidified with dilute hydrochloric acid. This is followed by extraction with a mixture of 9 parts by volume of methylene chloride and 1 part by volume of ethanol. The extract is evaporated and the residue obtained is taken up in acetone and the hydrochloride of the desired product is precipitated out by the addition of ethereal hydrochloric acid. There are obtained 14.5 g. (59% of theory) 2-[3-(4-benzamidopiperidino)-propoxy]-benzoic acid hydrochloride; m.p. 207°-208° C.

Workup

  1. additionA mixture of 23.6 g
  2. temperatureunder reflux for 1 hour
  3. customevaporated
  4. dissolutionthe evaporation residue dissolved in water
  5. extractionThis is followed by extraction with a mixture of 9 parts by volume of methylene chloride and 1 part by volume of ethanol
  6. customThe extract is evaporated
  7. customthe residue obtained
  8. customthe hydrochloride of the desired product is precipitated out by the addition of ethereal hydrochloric acid
  9. customThere are obtained 14.5 g

Sources & evidence

ORD record
ord-7fa5a7291a474822b144ab8997f23967
Source dataset
uspto-grants-1982_09
Patent number
US04348401

Reaction notes

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