Thionyl Chloride → Tert-butyl 4-(cyano(phenyl)methylene)piperidine-1-carboxylate

HRID 1943024Notes

Reaction equation

HRID 1943024 reaction equation
[C:1]([CH:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:4]1(O)[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2].O=S(Cl)Cl>N1C=CC=CC=1>[C:1]([C:3]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[C:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1)#[N:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58415929Tert-butyl 4-[cyano(phenyl)methyl]-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 44122578Tert-butyl 4-(cyano(phenyl)methylene)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To tert-butyl 4-[cyano(phenyl)methyl]-4-hydroxypiperidine-1-carboxylate (1.8 g, 5.69 mmol) in pyridine (4 ml) was added SOCl2 (2.076 ml, 28.4 mmol) and the reaction was stirred for 10 min. The reaction mixture was concentrated in vacuo. The resulting crystalline solid was adsorbed onto silica gel and purified by silica gel chromatography in an Isco Companion. The desired fractions were combined and concentrated in vacuo. 1.18 g, 70% over two steps.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by silica gel chromatography in an Isco Companion
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bcee43b82db4cbd87de0f449560d258
Source dataset
uspto-grants-2013_03
Patent number
US08389720B2

Reaction notes

Loading…