Chloroacetyl chloride → 1-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl Chloroacetate

HRID 1493423Notes

Reaction equation

HRID 1493423 reaction equation
[CH:1]1([O:7][N:8]2[C:13]([CH3:15])([CH3:14])[CH2:12][CH:11]([OH:16])[CH2:10][C:9]2([CH3:18])[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:26][CH2:27][C:28](Cl)=[O:29]>ClCCl.C(OCC)C>[Cl:26][CH2:27][C:28]([O:16][CH:11]1[CH2:10][C:9]([CH3:18])([CH3:17])[N:8]([O:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:13]([CH3:14])([CH3:15])[CH2:12]1)=[O:29]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

Product 1

HCID 198313621-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl ChloroacetateYield 39%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 45.2 g (0.177 mol) of 1-cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidine, 17.9 g (0.177 mol) of triethylamine, and 150 ml of dichloromethane is added over a 1 hour interval at 5° C. to a solution of 20.0 g (0.177 mol) of chloroacetyl chloride in 100 ml of dichloromethane. The reaction mixture is stirred at ambient temperature for 1 hour and then diluted with diethyl ether (500 ml). Solids are removed by filtration, and the filtrate is washed with 1N hydrochloric acid (2×100 ml), saturated sodium bicarbonate solution (200 ml), and saturated sodium chloride solution (200 ml), then dried over magnesium sulfate and concentrated to obtain an oil. Purification by flash chromatography on silica gel (5:1 heptane: ethyl acetate) affords 22.6 g (39% yield) of the title compound, a white solid, mp 62°-4° C.

Workup

  1. customSolids are removed by filtration
  2. washthe filtrate is washed with 1N hydrochloric acid (2×100 ml), saturated sodium bicarbonate solution (200 ml), and saturated sodium chloride solution (200 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain an oil
  6. customPurification by flash chromatography on silica gel (5:1 heptane: ethyl acetate)

Sources & evidence

ORD record
ord-e8a95722e31941a5bfc0e6d6ed0b8ff5
Source dataset
uspto-grants-1991_06
Patent number
US05021478

Reaction notes

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