Oxalyl chloride → 1-Benzyl-4-thiophen-3-yl-piperidine-3-carbonyl chloride

HRID 30266Notes

Reaction equation

HRID 30266 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH:10]([C:19]([OH:21])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:25])=O>C(Cl)Cl.CN(C=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH:10]([C:19]([Cl:25])=[O:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 672078231-Benzyl-4-thiophen-3-yl-piperidine-3-carboxylic acid

Product 1

HCID 862292151-Benzyl-4-thiophen-3-yl-piperidine-3-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the product from step d) (4.68 g, 13.8 mmol) in CH2Cl2 (77 ml) was treated with DMF (3-4 drops) and oxalyl chloride (2.72 ml, 31 mmol) at 220C for 1 hour. Next, the solvent was evaporated providing the subtitle compound (4.38 g) that was used without further purification.

Workup

  1. customNext, the solvent was evaporated

Sources & evidence

ORD record
ord-b1718c701a464ab9aeb5b8602ffedecc
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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