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

HRID 1579358Notes

Reaction equation

HRID 1579358 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-d6960a34d7c44394880b4ae599881b6a
Source dataset
uspto-grants-1976_01
Patent number
US03931195

Reaction notes

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