Hydrochloric Acid → N-(1-benzylpiperid-4-yl)-2-hydroxy-4-amino-5-nitrobenzamide hydrochloride

HRID 1494532Notes

Reaction equation

HRID 1494532 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([NH:25]C(=O)C)=[CH:18][C:17]=2[O:29]C(=O)C)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:34].C(=O)(O)[O-].[Na+]>C(O)C.O>[ClH:34].[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([NH2:25])=[CH:18][C:17]=2[OH:29])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 12821304N-(1-benzylpiperid-4-yl)-2-acetoxy-4-acetamido-5-nitrobenzamide

Product 1

HCID 19828529N-(1-benzylpiperid-4-yl)-2-hydroxy-4-amino-5-nitrobenzamide hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A suspension of N-(1-benzylpiperid-4-yl)-2-acetoxy-4-acetamido-5-nitrobenzamide (4.5 g; 0.01 mol) [prepared by the procedure described in Example 1] in ethanol (25 ml), concentrated hydrochloric acid (4.5 ml) and water (50 ml) was boiled under reflux for 2 hours. The mixture was diluted with water, made alkaline with sodium bicarbonate and extracted with chloroform. The organic solution was dried (Na2SO4), the solvent removed in vacuo and the residue triturated with diethyl ether to give a solid which was treated with a saturated solution of hydrogen chloride in ethanol. After crystallization from ethanol, 3 g of N-(1-benzylpiperid-4-yl)-2-hydroxy-4-amino-5-nitrobenzamide hydrochloride were obtained, m.p. 248°-250° C. (dec).

Workup

  1. customprepared by the procedure
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with chloroform
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. customthe solvent removed in vacuo
  6. customthe residue triturated with diethyl ether
  7. customto give a solid which
  8. customAfter crystallization from ethanol

Sources & evidence

ORD record
ord-e216c34262aa47268c7c7f4d58680b76
Source dataset
uspto-grants-1991_06
Patent number
US05026858

Reaction notes

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