Thionyl Chloride → Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate

HRID 1020024Notes

Reaction equation

HRID 1020024 reaction equation
[C:1]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].S(Cl)([Cl:22])=O>>[CH2:4]([O:3][C:1]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([Cl:22])=[O:19])[CH2:13][CH2:12]1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Product 1

HCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate

Procedure

Piperidine-1,4-dicarboxylic acid monobenzyl ester (VI) (5.0 g, 19 mmol) was suspended in thionyl chloride (10 ml) and stirred at room temperature for one hour. Excess thionyl chloride was distilled out and the obtained crude 4-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester (VII) was used for the next reaction immediately.

Workup

  1. distillationExcess thionyl chloride was distilled out

Sources & evidence

ORD record
ord-798f23db83c54d67b2b589f92e7148f1
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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