Potassium Carbonate → 1-(3-Methoxy-4-nitro-benzyl)-piperidin-4-ol

HRID 1262311Notes

Reaction equation

HRID 1262311 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([O:12][CH3:13])[CH:4]=1.[NH:14]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:13][O:12][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[N+:9]([O-:11])=[O:10])[CH2:2][N:14]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 126216043-Methoxy-4-nitrobenzyl bromide

Product 1

HCID 667116861-(3-Methoxy-4-nitro-benzyl)-piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Into a 8-dram vial, 4-Bromomethyl-2-methoxy-1-nitro-benzene (2.44 g, 9.93 mmol), Piperidin-4-ol (2.01 g, 19.9 mmol), Potassium carbonate (5.49 g, 39.7 mmol), and N,N-Dimethylformamide (25 ml) were added. The reaction mixture was heated at 80° C. overnight. The reaction was partitioned with water and EtOAc. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with hexane and EtOAc as eluant (0 to 100% EtOAc). The collected fractions afforded 1-(3-Methoxy-4-nitro-benzyl)-piperidin-4-ol as a yellow solid.

Workup

  1. customThe reaction was partitioned with water and EtOAc
  2. customThe organic was separated
  3. washwashed with Brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe solid was filtered
  6. washwashed with DCM
  7. customThe solvent was removed under vacuum
  8. customThe reaction mixture was purified via ISCO column chromatography with hexane and EtOAc as eluant (0 to 100% EtOAc)

Sources & evidence

ORD record
ord-ec91ab89b2894839a1ed837692d51076
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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