4-Methylmorpholine → (1-(2-Methoxyethyl)piperidin-4-yl)methyl 4-nitrophenyl carbonate

HRID 417948Notes

Reaction equation

HRID 417948 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]1.CN1CCOCC1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:22]>C(Cl)Cl>[C:21](=[O:22])([O:23][C:24]1[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=1)[O:12][CH2:11][CH:8]1[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 28063614[1-(2-Methoxyethyl)piperidin-4-yl]methanol

Product 1

HCID 57955470(1-(2-Methoxyethyl)piperidin-4-yl)methyl 4-nitrophenyl carbonateYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-(2-methoxyethyl)piperidin-4-yl)methanol (3.65 g, 21.1 mmol) and NMM (2.5 mL, 22.8 mmol) in DCM (100 mL) at 0° C. was added p-nitrophenyl chloroformate. The reaction mixture was stirred at room temperature overnight and then washed sequentially with sat aq NaHCO3 solution (5×100 mL), dried (MgSO4) and concentrated in vacuo. The resulting orange oil was recrystallised from EtOAc and heptane to give (1-(2-methoxyethyl)piperidin-4-yl)methyl 4-nitrophenyl carbonate (3.65 g, 51%) as an orange solid.

Workup

  1. washwashed sequentially with sat aq NaHCO3 solution (5×100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting orange oil was recrystallised from EtOAc and heptane

Sources & evidence

ORD record
ord-20d8f3d7cb63441686c334ea77cc1461
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Reaction notes

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