Dichloromethane → ethyl 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylate

HRID 551791Notes

Reaction equation

HRID 551791 reaction equation
[I-].[N:2]1([C:12]([N:14]2[CH:18]=[CH:17][N+](C)=[CH:15]2)=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.ClCCl.N1CC[CH:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:25]C1>C(N(CC)CC)C>[N:2]1([C:12]([N:14]2[CH2:15][CH2:25][CH:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:17][CH2:18]2)=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70770Ethyl 4-piperidinecarboxylateHCID 109595761-(3,4-Dihydroquinolin-1(2H)-ylcarbonyl)-3-methyl-1H-imidazol-3-ium Iodide

Product 1

HCID 67188549ethyl 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

16.5 g of 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)-3-methyl-1H-imidazol-3-ium iodide, 224 ml of dichloromethane and 8.45 g of ethyl isonipecotate, followed by 31.22 ml of triethylamine, are introduced into a 500 ml round-bottomed flask. The reaction medium is stirred at ambient temperature for 20 hours. The solvent is evaporated under reduced pressure and the residue is taken up in ethyl acetate and then washed with water. The organic phase is dried over sodium sulfate and the solvent is evaporated under reduced pressure to result in 15.2 g of ethyl 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylate.

Workup

  1. additionare introduced into a 500 ml round-bottomed flask
  2. customThe solvent is evaporated under reduced pressure
  3. washwashed with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customto result in 15.2 g of ethyl 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylate

Sources & evidence

ORD record
ord-fbfd70cf10784e6ea6e2b306b0312358
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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