Triethylamine → Octahydroquinoline-1-carboxylic acid 3-chloropropylamide

HRID 39218

Reaction equation

HRID 39218 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]=[C:6]=[O:7].CCN(CC)CC.[NH:15]1[CH:24]2[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:18][CH2:17][CH2:16]1.CCOC(C)=O>C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([N:15]1[CH:24]2[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:18][CH2:17][CH2:16]1)=[O:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 92911DecahydroquinolineHCID 166752Propane, 1-chloro-3-isocyanato-

Product 1

HCID 66795223Octahydroquinoline-1-carboxylic acid 3-chloropropylamideYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.5 g (21 mmol) of 3-chloropropylisocyanate are dissolved in 150 mL of anhydrous THF and 6.4 mL (46 mmol) of Et3N. Once dissolved 3.4 mL (23 mmol) of decahydroquinoline are slowly added and it is refluxed for 18 h. AcOEt is then added and the resulting solution is sequentially washed with water, 1N HCl and brine. The organic phase is dried over anhydrous Na2SO4, it is filtered and the solvent is evaporated under reduced pressure yielding 4.6 g of intermediate IIIf.1. Method B: tr: 3.58 min; m/z: 259

Workup

  1. temperatureit is refluxed for 18 h
  2. washthe resulting solution is sequentially washed with water, 1N HCl and brine
  3. dry with materialThe organic phase is dried over anhydrous Na2SO4, it
  4. filtrationis filtered
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-815daed69aa74be79cf96e08165c9842
Source dataset
uspto-grants-2013_09
Patent number
US08524894B2

Linked notes

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