Formaldehyde → HCID 58995043, compound

HRID 536961Notes

Reaction equation

HRID 536961 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:16][NH2:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:18]=O>C(Cl)Cl.CCOC(C)=O>[CH3:18][NH:17][CH2:16][C:10]1([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 16641709HCID 16641709, compound

Product 1

HCID 58995043HCID 58995043, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of C-[4-(4-nitro-phenyl)-tetrahydro-pyran-4-yl]-methylamine (as prepared in Example 73, step (b)) in DCM is treated with formaldehyde according to the literature procedure found in J. Org. Chem., 61, 3849-3862, (1996). The mixture is diluted with EtOAc and washed with water. The organic layer is dried (MgSO4) and concentrated in vacuo. The residue is purified by silica gel chromatography with the appropriate solvent to afford the title compound.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel chromatography with the appropriate solvent

Sources & evidence

ORD record
ord-12e4231b20c84c2bb70bb9581425e8a5
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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