Butyryl chloride → HCID 43422408, compound

HRID 2389483Notes

Reaction equation

HRID 2389483 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.[OH-].[Na+].[C:11](Cl)(=[O:15])[CH2:12][CH2:13][CH3:14]>O>[OH:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:11](=[O:15])[CH2:12][CH2:13][CH3:14])[CH2:2]1

Participants

5

Reactant 3

HCID 8855Butyryl chlorideHCID 14798Sodium HydroxideHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 43422408HCID 43422408, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of piperidin-3-yl-methanol (2.3 g, 20 mmol) in water (30 ml) is slowly added NaOH (1.2 g, 30 mmol). After total dissolution butyryl chloride (2.15 g, 2.11 ml, 20.2 mmol) is slowly added dropwise. The resulting mixture is allowed to stir overnight at rt. The water phase is extracted three times with dichloromethane. The combined organic phases are washed with brine and dried over Na2SO4. The solvents are evaporated in vacuo yielding the title compound (2.48 g) in 66% as a colourless oil which solidifies on standing: tR=1.52 min (LC-2), ESI-MS (pos.): m/z 208.00 [M+Na]+; 1H-NMR (CDCl3): The product is a (1:1) mixture of rotamers: δ (ppm) 0.92 (t, 3H, CH3), 1.21 (m, 0.5H), 1.33-1.52 (m, 2H), 1.57-1.84 (m, 5H), 2.26-2.32 (m, 2H, CH2C═O), 2.74 (dt, 0.5H), 2.87 (dd, 0.5H), 3.10 (dd, 1H), 3.26 (ddd, 1H), 3.39-3.45 (m, 1.5H), 3.51-3.59 (m, 1H), 3.91 (dd, 1H), 4.29 (dt, 0.5H).

Workup

  1. additionis slowly added dropwise
  2. extractionThe water phase is extracted three times with dichloromethane
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvents are evaporated in vacuo

Sources & evidence

ORD record
ord-b45b95d34d4d47c1a5c173d9579b4794
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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