Triethylamine → Benzyl [1-(3,3-dimethyl-2-oxobutyl)piperidin-4-yl]methylcarbamate

HRID 965791

Reaction equation

HRID 965791 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30]>CN(C)C=O>[CH3:30][C:29]([CH3:32])([CH3:31])[C:28](=[O:33])[CH2:27][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21642BromopinacoloneHCID 14809798Benzyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 86759854Benzyl [1-(3,3-dimethyl-2-oxobutyl)piperidin-4-yl]methylcarbamateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyl piperidin-4-ylmethylcarbamate (Tetrahedron Lett. 1990, 31, 6903, 6.9 g, 27.8 mmol) in N,N-dimethylformamide (60 mL) were added triethylamine (9.7 mL, 69.5 mmol) and 1-bromo-3,3-dimethylbutan-2-one (7.9 g, 41.7 mmol) at room temperature. The mixture was stirred at room temperature for 2 h and quenched with water (60 mL) followed by extraction with ethyl acetate-toluene mixture (3×30 mL). Concentration and purification by column chromatography on silica gel eluting with ethyl acetate/hexane (2:1) gave the title compound (9.6 g, 100%) as a pale yellow solid.

Workup

  1. customquenched with water (60 mL)
  2. extractionfollowed by extraction with ethyl acetate-toluene mixture (3×30 mL)
  3. concentrationConcentration and purification by column chromatography on silica gel eluting with ethyl acetate/hexane (2:1)

Sources & evidence

ORD record
ord-59257743e704426aa36095b637a36c73
Source dataset
uspto-grants-2005_10
Patent number
US06951867B2

Linked notes

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