Thionyl Chloride → 1-Acetylpiperidine-4-carbonyl chloride

HRID 324546Notes

Reaction equation

HRID 324546 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=11.4 Hz, 1H), 3.036 (t, J=11.4 Hz, 1H), 3.692 (d, J=13.2 Hz, 1H), 4.144 (d, J=13.2 Hz, 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-7349247291604dbfa474ffa0db284c86
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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