Thionyl Chloride → 1-Acetylpiperidine-4-carbonyl chloride

HRID 1861769Notes

Reaction equation

HRID 1861769 reaction equation
[C:1]([N:4]1[CH2:12][CH2:11][CH:7]([C:8](O)=[O:9])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].O=S(Cl)[Cl:15]>>[C:1]([N:4]1[CH2:12][CH2:11][CH:7]([C:8]([Cl:15])=[O:9])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 1172551-Acetylpiperidine-4-carboxylic acid

Product 1

HCID 1009501-Acetylpiperidine-4-carbonyl chlorideYield 97%

Procedure

N-acetylisonipecotic acid (0.67 g, 3.9 mmol) was added to SOCl2 (4.1 mL). The acid chloride precipitated from solution and petrol (60 mL) was added. The mixture was filtered and the residue was washed several times with petrol to afford the title compound as a white solid (0.716 g, 97%). m.p. 133-138° C. 1H NMR (DMSO): 1.2-1.5 (m, 2H), 1.65-2.0 (m, 2H), 1.94 (s, 3H), 2.3-2.5 (m, 1H), 2.639 (t, J=11.4Hz, 1H), 3.036 (t, J=11.4Hz, 1H), 3.692 (d, J=13.2Hz, 1H), 4.144 (d, J=13.2Hz, 1H). IR (KBr): 1789, 1745, 1660 (cm−1). MS (m/z): 189, 126, 146, 84.

Workup

  1. customThe acid chloride precipitated from solution and petrol (60 mL)
  2. additionwas added
  3. filtrationThe mixture was filtered
  4. washthe residue was washed several times with petrol

Sources & evidence

ORD record
ord-07d93f7ac2fe497a9b3cf5eca00d435d
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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