Ethanol → tert-Butyl {[1-(ethoxymethyl)piperidin-4-yl]methyl}carbamate

HRID 645969Notes

Reaction equation

HRID 645969 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.C=O.[C:18](=[O:21])([O-])[O-].[K+].[K+].[CH2:24](O)[CH3:25]>>[CH2:24]([O:21][CH2:18][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3][CH2:2]1)[CH3:25]

Participants

5

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 67233964tert-Butyl {[1-(ethoxymethyl)piperidin-4-yl]methyl}carbamate

Procedure

To a stirred solution of tert-butyl (piperidin-4-ylmethyl)carbamate (7.0 g, 33 mmol) in ethanol (19 mL), paraformaldehyde (1.2 g, 39 mmol) and potassium carbonate (5.4 g, 39 mmol) were added at ambient temperature. The mixture was stirred at ambient temperature for 4 h. The mixture was filtered and the filter cake was washed with ethanol (50 mL). The volatile components were removed by evaporation to give the title compound 8.9 g (quant.) as a white powder.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with ethanol (50 mL)
  3. customThe volatile components were removed by evaporation

Sources & evidence

ORD record
ord-697313f6594a4c77aa7ccf6ebcef80e8
Source dataset
uspto-grants-2010_04
Patent number
US07705020B2

Reaction notes

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