4-Methylmorpholine → 1-Methylpiperidin-4-yl 4-nitrophenyl carbonate

HRID 417965Notes

Reaction equation

HRID 417965 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.CN1CCOCC1.Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:18]>C(Cl)Cl>[C:17](=[O:18])([O:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1)[O:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 660484-Piperidinol, 1-methyl-HCID 821294-Nitrophenyl chloroformate

Product 1

HCID 666506911-Methylpiperidin-4-yl 4-nitrophenyl carbonateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-1-methyl piperidine (3.00 g, 26.1 mmol) and NMM (3.0 mL, 27.3 mmol) in DCM (50 mL) at 0° C. was added p-nitrophenyl chloroformate (5.51 g, 27.4 mmol). The reaction mixture was stirred at room temperature for 4 hours, and a cream precipitate gradually formed. The reaction mixture was filtered and the residue was washed with DCM (50 mL) to give 1-methylpiperidin-4-yl 4-nitrophenyl carbonate (7.24 g, 99%) as a cream solid.

Workup

  1. customa cream precipitate gradually formed
  2. filtrationThe reaction mixture was filtered
  3. washthe residue was washed with DCM (50 mL)

Sources & evidence

ORD record
ord-edf27c8575614917b6c7e67506ffcd64
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Reaction notes

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