Hydrochloric Acid → 2-[4-(2-Hydroxyethylamino)piperidin-1-yl]-5-nitrobenzonitrile

HRID 1744535Notes

Reaction equation

HRID 1744535 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10])([O-:3])=[O:2].[OH:19][CH2:20][CH2:21][NH2:22].C([BH3-])#N.[Na+].Cl>O1CCCC1.CO>[OH:19][CH2:20][CH2:21][NH:22][CH:15]1[CH2:16][CH2:17][N:12]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][C:8]=2[C:9]#[N:10])[CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 5003444Sodium cyanoborohydrideHCID 222279875-Nitro-2-(4-oxopiperidin-1-yl)benzonitrile

Product 1

HCID 222280232-[4-(2-Hydroxyethylamino)piperidin-1-yl]-5-nitrobenzonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Nitro-2-(4-oxopiperidin-1-yl)benzonitrile (5.0 g), 2-hydroxyethylamine (1.5 g) and sodium cyanoborohydride (1.3 g) were added to a mixed solvent of methanol (100 ml) and tetrahydrofuran (50 ml) and the mixture was stirred at room temperature for 1 h. An aqueous hydrochloric acid solution was added to keep the reaction mixture acidic. The solvent was evaporated under reduced pressure. Aqueous sodium hydroxide solution was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow precipitation, whereby the title compound (3.6 g) was obtained, melting point: 115° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionAqueous sodium hydroxide solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customafter which the solvent was evaporated under reduced pressure
  7. additionDiisopropyl ether was added to the residue
  8. customprecipitation, whereby the title compound (3.6 g)
  9. customwas obtained

Sources & evidence

ORD record
ord-e98d02d096044da9b509756462ea2640
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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