4-Methylmorpholine → HCID 66651361, compound

HRID 417980Notes

Reaction equation

HRID 417980 reaction equation
[N+](C1C=[CH:8][C:7]([O:10][C:11](=[O:22])[O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=CC=1)([O-])=O.OCC[N:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]1.CN1CCOCC1>C(Cl)Cl>[C:11](=[O:22])([O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)[O:10][CH2:7][CH2:8][N:26]1[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 78756Bis(4-nitrophenyl) carbonateHCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate

Product 1

HCID 66651361HCID 66651361, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bis(p-nitrophenyl)carbonate (1.52 g, 5.0 mmol) was dissolved in DCM (20 mL). tert-Butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate from the previous step (1.15 g, 5.0 mmol) and NMM (0.55 mL, 5.0 mmol) were added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with DCM (40 mL) and washed with sat aq NaHCO3 solution (5×50 mL), dried (Na2SO4) and concentrated in vacuo to give a yellow oil. The oil was purified by recrystallisation from EtOAc and heptane to give 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)ethyl 4-nitrophenyl carbonate (1.208 g, 61%) as an orange solid.

Workup

  1. washwashed with sat aq NaHCO3 solution (5×50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto give a yellow oil
  5. customThe oil was purified by recrystallisation from EtOAc and heptane

Sources & evidence

ORD record
ord-81c2fa758b944001a0b29c8fecea54e4
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Reaction notes

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