Water → HCID 10830499, compound

HRID 366520Notes

Reaction equation

HRID 366520 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([N+:25]([O-])=[O:26])[CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>CCO.Cl.[Fe]>[NH4+:11].[OH-:26].[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]#[C:17][C:18]2[CH:19]=[C:20]([NH2:25])[C:21]([NH2:24])=[CH:22][CH:23]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 962WaterHCID 10808715HCID 10808715, compound

Product 2

HCID 14923Ammonium HydroxideHCID 10830499HCID 10830499, compoundYield 155.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

4-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-2-nitro-phenylamine (crude product, example 69) (2.56 g, 7.0 mmol) is stirred in EtOH (52 mL) and water (8 mL) with conc. HCl (5 drops) and iron filings (3.75 g) at 75° C. for 2 hr. The mixture is filtered and evaporated. The residue is purified by medium-pressure column chromatography on silica gel eluting with 200:8:1 CH2Cl2 :EtOH:NH4OH to give the title compound as a beige solid (1.82 g): mp 141-142° C.

Workup

  1. filtrationThe mixture is filtered
  2. customevaporated
  3. customThe residue is purified by medium-pressure column chromatography on silica gel eluting with 200:8:1 CH2Cl2

Sources & evidence

ORD record
ord-8dfde19298fe47fda0da9085553bfeb7
Source dataset
uspto-grants-2000_10
Patent number
US06130234

Reaction notes

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