HCID 178418361, compound → HCID 178512490, compound

HRID 1600688Notes

Reaction equation

HRID 1600688 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH:15]3[CH2:20][CH2:19][CH:18]([N:21](C(OCC4C=CC=CC=4)=O)[C:22]([NH:24]C(OCC4C=CC=CC=4)=O)=[NH:23])[CH2:17][CH2:16]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>CO.[Pd]>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH:15]3[CH2:20][CH2:19][CH:18]([NH:21][C:22]([NH2:24])=[NH:23])[CH2:17][CH2:16]3)[CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178512421HCID 178512421, compound

Product 1

HCID 178512490HCID 178512490, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Trans-N-{4-[2-(4-phenyl-piperazin-1-yl)-ethyl]cyclohexyl-N,N'-dicarbobenzyloxyguanidine (2.77 g, 4.63 mol) was hydrogenolyzed in MeOH (250 mL) under 48 psi hydrogen pressure in the presence of 20% palladium on carbon catalyst (0.25 g). Filtration of the reaction mixture, evaporation of the filtrate, and recrystallization of the residue from isopropanol (i-PrOH)-Et2O yielded 1.39 g (91%) of the product; mp 140-170° C.

Workup

  1. filtrationFiltration of the reaction mixture, evaporation of the filtrate, and recrystallization of the residue from isopropanol (i-PrOH)-Et2O

Sources & evidence

ORD record
ord-3cfc34a5a5f04908bd544f282028bbd6
Source dataset
uspto-grants-1999_11
Patent number
US05977110

Reaction notes

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