Water → N-{2-[2-(1-Ethylpiperidin-2-yl)ethyl]phenyl}formamide

HRID 461909Notes

Reaction equation

HRID 461909 reaction equation
[I-].[CH2:2]([N+:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][CH:19]=[O:20])[CH3:3].[OH-].[Na+].O.[BH4-].[Na+]>CO>[CH2:2]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][CH:19]=[O:20])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 205600501-Ethyl-2-[2-(2-formamidophenyl)ethyl]pyridin-1-ium iodide

Product 1

HCID 20559971N-{2-[2-(1-Ethylpiperidin-2-yl)ethyl]phenyl}formamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-ethyl-2-(o-formamidophenethyl)pyridinium iodide (44.8 g., 0.117 mole), 50% NaOH (11.2 g., 0.14 mole), and water (40 ml.) in methanol (330 ml.) is added portionwise NaBH4 (5.32 g., 0.14 mole). The solution is stirred for 2 hr. and evaporated. Water is added to the residue thus obtained and the mixture extracted with ether. The ethereal extracts are dried (MgSO4) and evaporated. The residue taken up in 200 ml. of ethanol and hydrogenated in a Parr apparatus using 5 g. of 10% palladium on carbon as catalyst affords 1-ethyl-2-(2-formamidophenethyl)piperidine.

Workup

  1. customand evaporated
  2. additionWater is added to the residue
  3. customthus obtained
  4. extractionthe mixture extracted with ether
  5. dry with materialThe ethereal extracts are dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-d84f4b5a799a43acade4aa4e3bc626b5
Source dataset
uspto-grants-1977_12
Patent number
US04064254

Reaction notes

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