Formaldehyde → Benzyl [3-methoxy-4-(1-methylpiperidin-4-yl)phenyl]carbamate

HRID 869254Notes

Reaction equation

HRID 869254 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C=O.[C:28](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O.ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:10][CH2:11][N:12]([CH3:28])[CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86662054Benzyl (3-methoxy-4-piperidin-4-ylphenyl)carbamate

Product 1

HCID 86662055Benzyl [3-methoxy-4-(1-methylpiperidin-4-yl)phenyl]carbamateYield 79.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a mixture of benzyl (3-methoxy-4-piperidin-4-ylphenyl)carbamate (Preparation Example 455) (1.52 g) and 1,2-dichloroethane (70 mL), formalin (3.62 mL) and sodium triacetoxyborohydride (1.42 g) were added and stirred overnight at room temperature. After addition of water and saturated aqueous sodium hydrogen carbonate, the reaction liquid was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (eluent; chloroform:methanol:saturated aqueous ammonia=100:0:0 to 10:1:0.1) to give benzyl [3-methoxy-4-(1-methylpiperidin-4-yl)phenyl]carbamate (1.26 g) as a white solid.

Workup

  1. additionwere added
  2. customthe reaction liquid
  3. extractionwas extracted with chloroform
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:saturated aqueous ammonia=100:0:0 to 10:1:0.1)

Sources & evidence

ORD record
ord-541203a8e55e4ecbb8cd6527c5d3dcd2
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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