Lawesson's reagent → 2-Thioxo-[1,4']bipiperidinyl-1'-carboxylic acid benzyl ester

HRID 2221076Notes

Reaction equation

HRID 2221076 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2=[S:33])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 23369980HCID 23369980, compound

Product 1

HCID 233699572-Thioxo-[1,4']bipiperidinyl-1'-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Oxo-[1,4′]bipiperidinyl-1′-carboxylic acid benzyl ester (3.1 g) in tetrahydrofuran (10 mL) was added to a suspension of Lawesson's Reagent (1.98 g) in tetrahydrofuran (40 mL). After 20 minutes the reaction was concentrated and the resulting gum was subjected to chromatography with methylene chloride: ether (gradient 10:1, 5:1) as eluent. The title compound was obtained as a white foam (2.9 g). Rf=0.42 in methylene chloride:ether (10:1). MS: m/z=333 (M+H).

Workup

  1. concentrationAfter 20 minutes the reaction was concentrated

Sources & evidence

ORD record
ord-a75f51c9885549a58a8d7ac9dc6da543
Source dataset
uspto-grants-2008_05
Patent number
US07368461B2

Reaction notes

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