Ethyl Acetate → HCID 68693305, compound

HRID 1296291Notes

Reaction equation

HRID 1296291 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:11]([CH3:21])[CH2:10][N:9]1[C:22](OC)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CCOC(C)=O>C(Cl)Cl>[CH2:14]([N:12]1[C@@H:11]([CH3:21])[CH2:10][N:9]2[C:22](=[O:23])[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH2:1][C@@H:8]2[CH2:13]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 68688953HCID 68688953, compound

Product 1

HCID 68693305HCID 68693305, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of (2S,5R)-methyl 2,4-dibenzyl-5-methylpiperazine-1-carboxylate (0.28 g, 0.83 mmol), phosphorous oxychloride (5.0 ml) and phosphorous pentoxide (0.48 g, 1.6 mmol) was stirred at 100° C. under nitrogen overnight. The reaction was removed from the heat, quenched with ice, and brought to pH 7 to 8 with 1 N NaOH. Extraction with EtOAc (3×) and washing the combined organic layers with brine and drying over MgSO4 afforded 0.11 g of crude product after evaporation of the solvent. Flash chromatography (SiO2, CH2Cl2 to 60% EtOAc in CH2Cl2) afforded pure product (47 mg, 19% yield). MS (ESI) 307 (M+H).

Workup

  1. customThe reaction was removed from the heat
  2. customquenched with ice
  3. extractionExtraction with EtOAc (3×)
  4. washwashing the combined organic layers with brine
  5. dry with materialdrying over MgSO4
  6. customafforded 0.11 g of crude product
  7. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-844a4b94c2a24aefbc0a60ce83be03d1
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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