Acetyl chloride → 1-(4-Hydroxypiperidin-1-yl)ethan-1-one

HRID 591709Notes

Reaction equation

HRID 591709 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[C:15](Cl)(=[O:17])[CH3:16]>C1COCC1>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:15](=[O:17])[CH3:16])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 79341Piperidin-4-ol

Product 1

HCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxypiperidine (5.00 g, 49.4 mmol) in anhydrous THF (30 mL) and triethylamine (10 mL, 75 mmol) was added acetyl chloride (3.52 mL, 49.4 mmol). After the addition, the mixture was stirred for another 2 hours at room temperature. The solid formed was filtered and the mother liquid was concentrated to yield 5.0 g of crude product, which was purified by column chromatography on silica gel (230-400 mesh), using 5% methanol in dichloromethane as eluent, to give 1-(4-hydroxy-piperidin-1-yl)-ethanone. Yield: 2.40 g (34%).

Workup

  1. additionAfter the addition
  2. customThe solid formed
  3. filtrationwas filtered
  4. concentrationthe mother liquid was concentrated
  5. customto yield 5.0 g of crude product, which
  6. customwas purified by column chromatography on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-2c401801d0664aa495c018c3913e27e8
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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