Thiophene → Ethyl cis-4-[(5-amino-4-chloro-2-methoxybenzoyl)amino]-3-methoxy-1-piperidinecarboxylate

HRID 981304Notes

Reaction equation

HRID 981304 reaction equation
[Cl:1][C:2]1[C:23]([N+:24]([O-])=O)=[CH:22][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][C@H:10]2[O:20][CH3:21])=[O:7])=[C:4]([O:27][CH3:28])[CH:3]=1.S1C=CC=C1.[H][H]>CO.[Pt]>[NH2:24][C:23]1[C:2]([Cl:1])=[CH:3][C:4]([O:27][CH3:28])=[C:5]([CH:22]=1)[C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][C@H:10]1[O:20][CH3:21])=[O:7]

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 67928767HCID 67928767, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67928779Ethyl cis-4-[(5-amino-4-chloro-2-methoxybenzoyl)amino]-3-methoxy-1-piperidinecarboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 90.5 parts of ethyl cis-4-[(4-chloro-2-methoxy-5-nitrobenzoyl)amino]-3-methoxy-1-piperidinecarboxylate, 3 parts of a solution of thiophene in methanol 4% and 400 parts of methanol was hydrogenated at normal pressure and at 50° C. with 5 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 crystallized from 2-propanol. The product was filtered off and dried, yielding 80 parts (94%) of ethyl cis-4-[(5-amino-4-chloro-2-methoxybenzoyl)amino]-3-methoxy-1-piperidinecarboxylate: mp. 142.5° C. (interm. 14).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from 2-propanol
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-5a421704462c4aab8f8178eddca63923
Source dataset
uspto-grants-1991_02
Patent number
US04990521

Reaction notes

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