Tetrahydrofuran → HCID 21500239, compound

HRID 1729799Notes

Reaction equation

HRID 1729799 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH:10]2[CH3:19])=[C:4]([N+:20]([O-])=O)[CH:3]=1.O1CCCC1.[H][H]>[Ni].CO>[NH2:20][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH:10]1[CH3:19]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 21500238HCID 21500238, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21500239HCID 21500239, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 51 parts of methyl 4-(4-chloro-2nitrophenylamino)-3-methyl-1-piperidinecarboxylate, 270 parts of tetrahydrofuran and 96 parts of methanol is hydrogenated at normal pressure and at normal temperature with 15 parts of raney-nickel catalyst. After the calculated amount of hydrogen is taken up (6 hours), the catalyst is filtered off and the filtrate is evaporated. The oily residue is triturated in warm 2,2'-oxybispropane. After cooling, the product is filtered off, pulverized in a mortar and triturated again in 2,2'-oxybispropane. The product is filtered off and dried, yielding methyl 4-(2-amino-4-chlorophenylamino)-3-methyl-1-piperidinecarboxylate.

Workup

  1. custom(6 hours)
  2. filtrationthe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customThe oily residue is triturated in warm 2,2'-oxybispropane
  5. temperatureAfter cooling
  6. filtrationthe product is filtered off
  7. customtriturated again in 2,2'-oxybispropane
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-0b4e727fb1064a0da3e95600876c145d
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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