4-Nitrobenzaldehyde → HCID 58775945, compound

HRID 1715332Notes

Reaction equation

HRID 1715332 reaction equation
[BH-](O[C:11]([CH3:13])=[O:12])(OC(C)=O)OC(C)=O.[Na+].[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)([O-:17])=[O:16].O1[CH2:31][CH2:30][CH:29]([NH:32][CH3:33])CC1.[CH2:34]=O.[OH-].[Na+]>C(O)(=O)C.C(Cl)Cl>[CH3:33][N:32]([CH2:22][C:21]1[CH:24]=[CH:25][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=1)[CH2:29][CH:30]1[CH2:13][CH2:11][O:12][CH2:34][CH2:31]1

Participants

8

Reactant 5

HCID 5414-NitrobenzaldehydeHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydride2×HCID 69919504-(Methylamino)tetrahydro-2H-pyran

Product 1

HCID 58775945HCID 58775945, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

NaB(OAc)3H (3.5 mmol, 0.75 g) was added to a mixture of 4-nitro-benzaldehyde Compound 4a (2.8 mmol, 0.42 g), (tetrahydro-pyran-4-yl)-methylamine Compound 4b (3.0 mmol, 0.35 g) and glacial acetic acid (3 drops) in CH2Cl2 (50 mL) and the resulting suspension was stirred at r.t. overnight. An aliquot of the reaction mixture showed the formation of product (MS m/e 251; 100%). An aqueous solution of formaldehyde (37% solution, 9.6 mmol, 0.8 mL) was added, followed by NaB(OAc)3H (3.5 mmol, 0.75 g). The reaction mixture was stirred at r.t. for 2 h, then made basic with a 2N NaOH solution and extracted with CH2Cl2. The organic layer was washed with brine, then separated and dried over Na2SO4. The drying agent was filtered and the solvent was removed in vacuo to yield methyl-(4-nitro-benzyl)-(tetrahydro-pyran-4-ylmethyl)-amine Compound 4c as yellow oil (0.63 g, 85% yield). MS m/e 265 (M+H, 100%).

Workup

  1. stirringThe reaction mixture was stirred at r.t. for 2 h
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with brine
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. filtrationThe drying agent was filtered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-299ad76554f34436814dcba0ef024d5d
Source dataset
uspto-grants-2010_09
Patent number
US07799824B2

Reaction notes

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