Ethanol → HCID 19092351, compound

HRID 487598Notes

Reaction equation

HRID 487598 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:33]=[CH:32][C:12]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH:24]=[C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:22][CH2:21]3)=[O:14])=[C:11]([N+:34]([O-])=O)[CH:10]=2)[CH2:4][CH2:3]1.C(O)C.[Sn](Cl)Cl.[OH-].[Na+]>C(Cl)(Cl)Cl.O1CCCC1>[NH2:34][C:11]1[CH:10]=[C:9]([CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:33]=[CH:32][C:12]=1[C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:21][CH:22]=[C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:24][CH2:25]1)=[O:14]

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 19092355HCID 19092355, compound

Product 1

HCID 19092351HCID 19092351, compoundYield 126.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 4-(4-methylpiperazin-1-ylmethyl)-2-nitro-N-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]benzamide (0.21 g), ethanol (5 ml) and dry tetrahydrofuran (10 ml) was added tin (II) chloride (0.33 g) and the mixture was refluxed for 1 hour. After cooling, chloroform (15 ml) and 1N sodium hydroxide (25 ml) were added and the mixture was stirred. The organic layer was separated and the remained aqueous layer was extracted with chloroform. The organic layer and extract were combined and dried over magnesium sulfate and evaporated to give 2-amino-4-(4-methylpiperazin-1-ylmethyl)-N-[4-(4-phenyl-1,2,3,6-tetrahydropyridin 1-yl)butyl]benzamide (0.25 g).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. customThe organic layer was separated
  4. extractionthe remained aqueous layer was extracted with chloroform
  5. extractionThe organic layer and extract
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-2f9ca79480c646b5a4e6a5a96d3f8137
Source dataset
uspto-grants-1994_03
Patent number
US05296487

Reaction notes

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