Carbon Tetrachloride → Ethyl 2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl]benzoate

HRID 1033996Notes

Reaction equation

HRID 1033996 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:15][C:16]([OH:18])=O)[CH:7]=[CH:8][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl.[CH3:50][CH:51]([CH3:67])[CH2:52][CH:53]([NH2:66])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=1[N:60]1[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]1>C(#N)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:15][C:16]([NH:66][CH:53]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=2[N:60]2[CH2:61][CH2:62][CH2:63][CH2:64][CH2:65]2)[CH2:52][CH:51]([CH3:67])[CH3:50])=[O:18])[CH:7]=[CH:8][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2]

Participants

7

Reactant 5

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 101312123-Ethoxy-4-ethoxycarbonylphenylacetic acidHCID 104220523-Methyl-1-(2-piperidino-phenyl)-1-butylamine

Product 1

HCID 13729227Ethyl 2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl]benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3 g (11.9 mmols) of 3-ethoxy-4-ethoxycarbonyl-phenylacetic acid, 3.7 g (14.3 mmols) of triphenylphosphine, 3.3 ml (23. 8 mmols) of triethylamine and 1.15 ml (11.9 mmols) of carbon tetrachloride were added successively to a solution of 2.9 g (11.9 mmols) of 3-methyl-1-(2-piperidino-phenyl)-1-butylamine in 29 ml of acetonitrile. The mixture was then stirred for 15 hours at room temperature, the solvent was removed in vacuo, and the residue was taken up in a mixture of ethyl acetate and water. The organic phase was dried over sodium sulfate, filtered and concentrated by evaporation in vacuo. The evaporation residue was purified by column chromatography on silica gel (toluene/acetone=10/1).

Workup

  1. customthe solvent was removed in vacuo
  2. additionthe residue was taken up in a mixture of ethyl acetate and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation in vacuo
  6. customThe evaporation residue was purified by column chromatography on silica gel (toluene/acetone=10/1)

Sources & evidence

ORD record
ord-264abf2b4f1b47388eec894c94b921c5
Source dataset
uspto-grants-1994_05
Patent number
US05312924

Reaction notes

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