Thionyl Chloride → HCID 63393068, compound

HRID 2389482Notes

Reaction equation

HRID 2389482 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9](=[O:13])[CH2:10][CH2:11][CH3:12])[CH2:4]1.O=S(Cl)[Cl:16]>C(Cl)(Cl)Cl>[Cl:16][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9](=[O:13])[CH2:10][CH2:11][CH3:12])[CH2:4]1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 43422408HCID 43422408, compound2×

Product 1

HCID 63393068HCID 63393068, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1-(3-hydroxymethyl-piperidin-1-yl)-butan-1-one (Starting material 1-01e, 1.33 g, 7.20 mmol) in dry chloroform (10 ml) is cooled down to 0° C. with an ice-water bath. A solution of SOCl2 (1.43 g, 876 μl, 12 mmol) in dry chloroform (10 ml) is added dropwise. The mixture is allowed to stir at reflux for 30 min. The solution is cooled down to rt, SOCl2 (0.48 g, 0.3 ml, 4.1 mmol) is added dropwise and the resulting solution is allowed to stir at reflux for another 30 min. Evaporation of the solvents under reduced pressure gives a brown liquid which is purified by column chromatography on silica-gel (AcOEt/heptane, 35:65), yielding the title compound (1.15 g) in 78% as a colourless liquid: 1H-NMR (CDCl3): The product is a (1:1) mixture of rotamers: δ (ppm) 0.95 (t, 3H, CH3), 1.33-1.54 (m, 2H), 1.58-1.95 (m, 3H), 1.68 (quint., 1H, CH2CH2CH3), 2.32 (dd, 2H, CH2C═O), 2.60 (t, 0.5H), 2.83 (t, 0.5H), 2.99 (m, 2H), 3.36-3.55 (m, 2H), 3.77 (d, 0.5H), 3.93 (d, 0.5H), 4.30 (d, 0.5H), 4.54 (d, 0.5H).

Workup

  1. temperatureat reflux for 30 min
  2. stirringto stir
  3. temperatureat reflux for another 30 min
  4. customEvaporation of the solvents under reduced pressure
  5. customgives a brown liquid which
  6. customis purified by column chromatography on silica-gel (AcOEt/heptane, 35:65)

Sources & evidence

ORD record
ord-111f82e8802e4f8aad5d0118ebd5a35b
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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