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

HRID 733094Notes

Reaction equation

HRID 733094 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C=O.[C:18]([O-:21])([O-])=O.[K+].[K+].[CH2:24](O)[CH3:25]>>[CH2:24]([O:21][CH2:18][N:12]1[CH2:11][CH2:10][CH:9]([CH2:8][NH:7][C:6](=[O:15])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:14][CH2:13]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 K2CO3 (5.4 g, 39 mmol) were added at ambient temperature. The mixture was stirred at ambident 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 8.9 g (quant.) of the title compound 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-5ccd384b08f446caa5e432dcef59f4c1
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

Loading…