HCID 67914555, compound → HCID 67914516, compound

HRID 345606Notes

Reaction equation

HRID 345606 reaction equation
[NH2:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]=[CH:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:11][C@H:10]2[O:26][CH3:27])=[O:7])=[C:4]([O:31][CH3:32])[CH:3]=1.[H][H]>[Pt].CO>[OH2:7].[NH2:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:11][C@H:10]2[O:26][CH3:27])=[O:7])=[C:4]([O:31][CH3:32])[CH:3]=1

Participants

5

Reactant 2

HCID 67914555HCID 67914555, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67914516HCID 67914516, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3.12 parts of cis-4-amino-5-chloro-N-[1-[4-(4-fluorophenyl)-3-butenyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide and 120 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was stirred in 1,1'-oxybisethane. The product was filtered off and dried, yielding 2.54 parts (81%) of cis-4-amino-5-chloro-N-[1-[4-(4-fluorophenyl)butyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide monohydrate; mp. 132.7° C. (compound 237).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. filtrationThe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-7e497bc03f40405a9c66671bb45e6229
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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