Carbon Tetrachloride → HCID 10815838, compound

HRID 1034009Notes

Reaction equation

HRID 1034009 reaction equation
[CH:1]1([CH2:7][CH:8]([NH2:21])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([CH2:36][C:37](O)=[O:38])[CH:28]=[CH:29][C:30]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl>C(#N)C>[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([CH2:36][C:37]([NH:21][CH:8]([CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:38])[CH:28]=[CH:29][C:30]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:23]

Participants

7

Reactant 5

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 101312123-Ethoxy-4-ethoxycarbonylphenylacetic acidHCID 10493480HCID 10493480, compound

Product 1

HCID 10815838HCID 10815838, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of α-cyclohexylmethyl-2-piperidino-benzylamine (1.13 g, 3.96 mmol) in acetonitrile (11 ml) are added, successively, 3-ethoxy-4-ethoxycarbonyl-phenyl acetic acid (1 g, 3.96 mmol), of triphenylphosphine (1.25 g, 4.76 mmol), triethylamine (1.11 ml, 7.92 mmol) and carbon tetrachloride (0.38 ml, 3.96 mmol) and the mixture is stirred for 15 hours at ambient temperature. It is then concentrated by evaporation in vacuo and partitioned between ethyl acetate and water. The organic extract is dried and filtered and concentrated by evaporation in vacuo. The evaporation residue is purified by column chromatography on silica gel (toluene/acetone=10/1).

Workup

  1. concentrationIt is then concentrated by evaporation in vacuo
  2. custompartitioned between ethyl acetate and water
  3. extractionThe organic extract
  4. customis dried
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation in vacuo
  7. customThe evaporation residue is purified by column chromatography on silica gel (toluene/acetone=10/1)

Sources & evidence

ORD record
ord-538e6bedb1cd41cb9e1324956c85109e
Source dataset
uspto-grants-1994_05
Patent number
US05312924

Reaction notes

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