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

HRID 1494533Notes

Reaction equation

HRID 1494533 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:28])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([NH2:25])=[CH:18][C:17]=2[O:26]C)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].[ClH:38]>C(Cl)Cl.O>[ClH:38].[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15](=[O:28])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([NH2:25])=[CH:18][C:17]=2[OH:26])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 12821241N-(1-Benzylpiperid-4-yl)-2-methoxy-4-amino-5-nitrobenzamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of N-(1-benzylpiperid-4-yl)-2-methoxy-4-amino-5-nitrobenzamide (3.8 g; 0.01 mol) [prepared as described in Example 1] in methylene chloride (70 ml) was added to another solution of boron tribromide (2.84 ml; 0.03 moles) in methylene chloride (20 ml). The mixture was stirred at room temperature for 24 hours and then poured into a mixture of a saturated solution of sodium bicarbonate in water (250 ml) and methylene chloride (100 ml). The decanted organic solution was dried and the solvent removed in vacuo to give a paste which was triturated with petroleum ether. The residue obtained was treated with a saturated solution of ethanolic hydrogen chloride to give 3 g of N-(1-benzylpiperid-4-yl)-2-hydroxy-4-amino-5-nitrobenzamide hydrochloride, m.p. 248°-250° C. (dec).

Workup

  1. customThe decanted organic solution was dried
  2. customthe solvent removed in vacuo
  3. customto give a paste which
  4. customwas triturated with petroleum ether
  5. customThe residue obtained

Sources & evidence

ORD record
ord-a77cbaabcde44d898821e9e163e341f4
Source dataset
uspto-grants-1991_06
Patent number
US05026858

Reaction notes

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