N-Methylbutylamine → HCID 23317083, compound

HRID 1982619Notes

Reaction equation

HRID 1982619 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][CH2:7][CH2:8]Cl)=[CH:4][CH:3]=1.[CH2:12]([NH:16][CH3:17])[CH2:13][CH2:14][CH3:15].C([O-])([O-])=O.[Na+].[Na+].[OH-].[K+]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][CH2:7][CH2:8][N:16]([CH3:17])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8068N-MethylbutylamineHCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 16096059HCID 16096059, compound

Product 1

HCID 23317083HCID 23317083, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

5.70 g of 2-(4-chloroanilino)ethylchloride, 5.28 g of n-butylmethylamine and 6.36 g of Na2CO3 were refluxed while stirring for approximately 24 hours in toluene as a solvent. After the addition of a solution of 1.80 g of 90% KOH in 15 ml of water the reaction mixture was extracted with diethyl ether. The ether layer was washed with water, dried and filtered. After evaporating the solvent approximately 6 g of product were obtained which was identified by means of thin layer chromatography. The product was purified via the HCl salt, after which 5.21 g of a light-brown oil were obtained; identification by means of N.M.R. spectrum.

Workup

  1. extractionwas extracted with diethyl ether
  2. washThe ether layer was washed with water
  3. customdried
  4. filtrationfiltered
  5. customAfter evaporating the solvent approximately 6 g of product
  6. customwere obtained which
  7. customThe product was purified via the HCl salt

Sources & evidence

ORD record
ord-a813d5d40da64081a1ae1bec397ababf
Source dataset
uspto-grants-1986_06
Patent number
US04596891

Reaction notes

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