Oxalyl chloride → HCID 15295470, compound

HRID 2210551Notes

Reaction equation

HRID 2210551 reaction equation
[CH:1]1([CH2:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:25])[C:22]([OH:24])=O)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.N.CC#[N:35]>CN(C=O)C.C1(C)C=CC=CC=1>[CH:1]1([CH2:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:25])[C:22]([NH2:35])=[O:24])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 15587892HCID 15587892, compoundHCID 19379067HCID 19379067, compound

Product 1

HCID 15295470HCID 15295470, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

Following the procedure of Example 9, 2-[4-(3-cyclopentylmethyl-4-methoxyphenyl)piperidin-1-yl]-2-oxo-acetic acid (2.2 mmol, 0.750 g), oxalyl chloride (2.42 mmol, 1.21 mL; 2M solution in CH2Cl2), DMF (4 drops), and saturated NH3 /CH3CN (22 mL) in dry toluene (22 mL) afforded a solid which was purified by flash chromatography (SiO2 : 40% EtOAc/hexane) to give the title compound as a white solid, mp=117°-118° C. (1.1 mmol, 0.388 g, 51%).

Workup

  1. customafforded a solid which
  2. customwas purified by flash chromatography (SiO2 : 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-175115a574f64f8e870dfe77037c60c8
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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