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

HRID 1856990Notes

Reaction equation

HRID 1856990 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-butylamin 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 silaca 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 silaca gel (toluene/acetone=10/1)

Sources & evidence

ORD record
ord-13b8c5f8b156426f8901b65771adda04
Source dataset
uspto-grants-2000_11
Patent number
US06143769

Reaction notes

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