Ethanol → N-(1-Methylhexyl)-N-(4,5-dihydro-2-thiazolyl)[(3-pyridyl)methyl]amine

HRID 1583566Notes

Reaction equation

HRID 1583566 reaction equation
[CH3:1][CH:2]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(O)C.Cl[CH2:20][CH2:21][N:22]=[C:23]=[S:24]>C(N(CC)CC)C>[CH3:1][CH:2]([N:8]([CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[C:23]1[S:24][CH2:20][CH2:21][N:22]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 702EthanolHCID 1386612-Chloroethyl IsothiocyanateHCID 147202823-(1-Methylhexylaminomethyl)pyridine

Product 1

HCID 13535583N-(1-Methylhexyl)-N-(4,5-dihydro-2-thiazolyl)[(3-pyridyl)methyl]amineYield 91%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 3.1 g. of N-(1-methylhexyl)-[(3-pyridyl)methyl]amine dissolved in approximately 20 ml. of ethanol-free chloroform was added 1.8 g. of 2-chloroethylisothiocyanate followed by 2.08 ml. of triethylamine. The reaction mixture was stirred at room temperature overnight and then refluxed for approximately 4 hours. The solvent was evaporated under reduced pressure and the residue was chromatographed over silica gel while eluting with chloroform/acetone to afford approximately 4.0 g. of the desired product. Yield 91%.

Workup

  1. temperaturerefluxed for approximately 4 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was chromatographed over silica gel
  4. washwhile eluting with chloroform/acetone
  5. customto afford approximately 4.0 g

Sources & evidence

ORD record
ord-78b3c458d6884f97bb8de9e5483ffc9c
Source dataset
uspto-grants-1985_11
Patent number
US04552886

Reaction notes

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