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

HRID 1974109Notes

Reaction equation

HRID 1974109 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-6936ce6228d64508b437eb159dda496f
Source dataset
uspto-grants-1976_12
Patent number
US04000143

Reaction notes

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