Ammonia → HCID 14854959, compound

HRID 654171Notes

Reaction equation

HRID 654171 reaction equation
[NH2:1][C:2]1[C:22]([Cl:23])=[CH:21][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]#[N:18])[CH2:11][C@H:10]2[O:19][CH3:20])=[O:7])=[C:4]([O:24][CH3:25])[CH:3]=1.N.[H][H]>[Ni].CO>[NH2:1][C:2]1[C:22]([Cl:23])=[CH:21][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][C@H:10]2[O:19][CH3:20])=[O:7])=[C:4]([O:24][CH3:25])[CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 67915944cis-4-amino-5-chloro-N-[1-(2-cyanoethyl)-3-methoxy-4-piperidinyl]-2-methoxybenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 14854959HCID 14854959, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3 parts of cis-4-amino-5-chloro-N[1-(2-cyanoethyl)-3-methoxy-4-piperidinyl]-2-methoxybenzamide and 200 parts of methanol, saturated with ammonia was hydrogenated at normal pressure and at 20° C. with 2 parts of Raney-nickel catalyst. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was dissolved in trichloromethane. The solution was washed with water, dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried in vacuo at 60° C., yielding 0.4 parts (13%) of cis-4-amino-N-[1-(3-aminopropyl)-3-methoxy-4piperidinyl]-5-chloro-2-methoxybenzamide; mp. 174.8 (interm. 3).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in trichloromethane
  4. washThe solution was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from acetonitrile
  9. filtrationThe product was filtered off
  10. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-3694ca7477cc4493af3eb01345aec5bb
Source dataset
uspto-grants-1992_07
Patent number
US05130312

Reaction notes

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