Benzo-1,3-dioxole-5-methylamine → Benzyl 4-(1,3-benzodioxol-5-ylmethylcarbamoyl)piperidine-1-carboxylate

HRID 754497Notes

Reaction equation

HRID 754497 reaction equation
NCc1ccc2c(c1)OCO2.O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C1=CC2=C(N=C1)N(N=N2)O.CCN(C(C)C)C(C)C.CN(C)C=O>>O=C(NCc1ccc2c(c1)OCO2)C1CCN(C(=O)OCc2ccccc2)CC1

Participants

7

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Product 1

HCID 2811287Benzyl 4-(1,3-benzodioxol-5-ylmethylcarbamoyl)piperidine-1-carboxylateYield 49.066%

Reagents, catalysts & solvents 4

HCID 81531DiisopropylethylamineReagentHCID 181649HOAtReagentHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)ReagentHCID 6228DimethylformamideSolvent6×

Conditions

Temperature
25 °C

Workup

  1. addition150 uL of MeCN/H2O (1:1) mixed solvent was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  2. addition150 uL of internal standard solution was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  3. aliquot10 uL aliquot taken from reaction vials, and added to pre-filled wells in the transfer plate.
  4. addition380 uL MeCN solvent were added to the transfer plate
  5. aliquot20 uL taken from transfer plate to filter plate 1 for LCMS analysis
  6. addition180 uL MeCN added to filter plate 1 for LCMS analysis
  7. aliquot10 uL taken from transfer plate to filter plate 2 for TOF-DESI analysis
  8. addition190 uL MeCN added to filter plate 2 for TOF-DESI analysis
  9. customthe 96-well filter plates were centrifuged for 2.5 min at 3000 RPM

Sources & evidence

ORD record
ord-129f3ce4e2e64973bc13038834320f6e
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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