Water → HCID 20560109, compound

HRID 1974093Notes

Reaction equation

HRID 1974093 reaction equation
[OH-].[Na+].O.[I-].[CH2:5]([N:7]([CH2:28][CH3:29])[C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][CH:26]=[O:27])=[N+:14]([CH3:16])[CH:15]=1)=[O:9])[CH3:6].[BH4-].[Na+]>CO>[CH2:28]([N:7]([CH2:5][CH3:6])[C:8]([CH:10]1[CH2:11][CH2:12][CH:13]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][CH:26]=[O:27])[N:14]([CH3:16])[CH2:15]1)=[O:9])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 20560000HCID 20560000, compound

Product 1

HCID 20560109HCID 20560109, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 50% sodium hydroxide solution (9.6 g., 0.12 mole) in 45 ml. of water is added to a solution of 5-diethylcarbamyl -2-(o-formamidophenethyl)-1-methylpyridinium iodide (46.7 g., 0.1 mole) in 300 ml. of methanol. Sodium borohydride (4.56 g., 0.12 mole) is added in portions with stirring to the reaction mixture. After 2 hr. the mixture is evaporated and water (500 ml.) is added to the resulting residue. This mixture is extracted with ether, the ethereal extracts washed with water, dried over magnesium sulfate and the ether evaporated. The resulting residue consisting of N,N-diethyl-6-(o-formamidophenethyl)-1-methyltetrahydropyridine-3-carboxamide hydrogenated in a Parr apparatus in 200 ml. of ethanol employing 4 g. of 10% palladium on carbon as the catalyst at a temperature of 50° -70° C. provides N,N-diethyl-6-(o-formamidophenethyl)-1-methylpiperidine-3-carboxamide.

Workup

  1. customthe mixture is evaporated
  2. additionwater (500 ml.) is added to the resulting residue
  3. extractionThis mixture is extracted with ether
  4. washthe ethereal extracts washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe ether evaporated

Sources & evidence

ORD record
ord-577580a08de441e4a2f503a057a74c93
Source dataset
uspto-grants-1976_12
Patent number
US04000143

Reaction notes

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