Thiophene → HCID 86744583, compound

HRID 981317Notes

Reaction equation

HRID 981317 reaction equation
[F:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][N:12]([CH:15]([CH3:35])[CH2:16][C:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[CH2:11][C@H:10]2[OH:36])=[O:7])=[C:4]([N+:39]([O-])=O)[CH:3]=1.S1C=CC=C1.[H][H]>CO.[Pt]>[OH2:7].[NH2:39][C:4]1[CH:3]=[C:2]([F:1])[CH:38]=[CH:37][C:5]=1[C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][N:12]([CH:15]([CH3:35])[CH2:16][C:17]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[CH2:11][C@H:10]1[OH:36])=[O:7]

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 86744585HCID 86744585, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86744583HCID 86744583, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 4 parts of trans-4-[(4-fluoro-2-nitrobenzoyl)amino]-3-hydroxy-N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide, 1 part of a solution of thiophene in methanol 4% and 200 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 to dry. The residue was taken up In acetonitrile. The organic layer was evaporated again and the residue was crystallized from a mixture of acetonitrile and a few drops of water. The product was filtered off and dried, yielding 1.93 parts (51.8%) of trans-4-[(2-amino-4-fluorobenzoyl)amino]-3-hydroxy-N,N,γ-trimethyl-α,α-diphenyl-1piperidinebutanamide monohydrate; mp. 127.0° C. (compound 67).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customto dry
  4. customThe organic layer was evaporated again
  5. customthe residue was crystallized from a mixture of acetonitrile and a few drops of water
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-4308036b09aa4ecdb09ee7d3c6265310
Source dataset
uspto-grants-1991_02
Patent number
US04990521

Reaction notes

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