Acetyl chloride → 1-(3-Hydroxypiperidin-1-yl)ethan-1-one

HRID 456450Notes

Reaction equation

HRID 456450 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.[C:15](Cl)(=[O:17])[CH3:16]>C1COCC1.C(Cl)Cl>[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:15](=[O:17])[CH3:16])[CH2:3]1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 232933-Hydroxypiperidine

Product 1

HCID 218970301-(3-Hydroxypiperidin-1-yl)ethan-1-oneYield 83.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-Hydroxypiperidine (3.0 g, 30.0 mmol) was dissolved in THF (40 mL) and methylene chloride (40 mL). Triethylamine (7.47 g, 74.0 mmol) was added. The mixture was cooled to −78° C. and acetyl chloride (2.35 g, 30.0 mmol) was added drop wise. The mixture was warmed to r.t. and stirred under nitrogen for 1 about an hour. The solvents were removed under reduced pressure, and the resulting oil was purified using silica chromatography (2% methanol in ethyl acetate) to afford the title compound (3.57 g, 83%) as an oil.

Workup

  1. temperatureThe mixture was warmed to r.t.
  2. customThe solvents were removed under reduced pressure
  3. customthe resulting oil was purified

Sources & evidence

ORD record
ord-ee7f708a522c4e49b678cf3f9f315113
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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