4-Methylmorpholine → (1-Methylpiperidin-4-yl)methyl 4-nitrophenyl carbonate

HRID 417945

Reaction equation

HRID 417945 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20](=O)[O:21]C2C=CC([N+]([O-])=O)=CC=2)=[CH:15][CH:14]=1)([O-:12])=[O:11].CN1CCOCC1>C(Cl)Cl>[C:20](=[O:21])([O:19][C:16]1[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:18][CH:17]=1)[O:9][CH2:8][CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 78756Bis(4-nitrophenyl) carbonateHCID 2719711-Methyl-4-piperidinemethanol

Product 1

HCID 57445006(1-Methylpiperidin-4-yl)methyl 4-nitrophenyl carbonateYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(1-Methylpiperidin-4-yl)methanol (2.50 g, 19.3 mmol) in DCM (50 mL) was added to a solution of bis-(4-nitrophenyl)carbonate (7.06 g, 23.2 mmol) in DCM (100 mL), followed by NMM (1.70 mL, 15.5 mmol). The reaction mixture was stirred for 90 hours and then washed sequentially with aliquots of 1 M aq Na2CO3 solution until the aqueous layer was colourless. The organic layer was dried (MgSO4) and concentrated in vacuo to give (1-methylpiperidin-4-yl)methyl 4-nitrophenyl carbonate (4.18 g, 73%) as a yellow solid.

Workup

  1. washwashed sequentially with aliquots of 1 M aq Na2CO3 solution until the aqueous layer
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-752a22679006497f8d1083d89e310ac5
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Linked notes

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