Formaldehyde → HCID 22989990, compound

HRID 1169372Notes

Reaction equation

HRID 1169372 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[O:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.[C:18](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:18][N:8]([CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH:14]1[CH2:15][CH2:16][O:11][CH2:12][CH2:13]1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 754524-MethoxybenzylamineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 22989990HCID 22989990, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Into a solution of 4-methoxybenzylamine (4.12 g) and tetrahydro-4H-pyran-4-one (3.00 g) in 1,2-dichloroethane (50 ml) was added sodium triacetoxyborohydride (6.99 g). After stirring at room temperature for 2 hours, 37% formalin solution (2.5 ml) and sodium triacetoxyborohydride (6.99 g) were added thereto. After stirring for additional one hour, the reaction mixture was mixed with an aqueous solution of sodium bicarbonate and was extracted with dichloromethane. The extract was washed with an aqueous solution of sodium chloride, was dried (anhydrous magnesium sulfate) and was then concentrated under reduced pressure. The residue was subjected to purification using silica gel column chromatography (ethyl acetate) to obtain N-methyl-N-(tetrahydropyran-4-yl)-4-methoxybenzylamine (3.56 g) as a light yellow, oily substance.

Workup

  1. stirringAfter stirring for additional one hour
  2. extractionwas extracted with dichloromethane
  3. washThe extract was washed with an aqueous solution of sodium chloride
  4. dry with materialwas dried (anhydrous magnesium sulfate)
  5. concentrationwas then concentrated under reduced pressure
  6. customThe residue was subjected to purification

Sources & evidence

ORD record
ord-a0e8bae8931f47b08e3ef4c53e29cd20
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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