Alimix → cis-4-amino-5-chloro-N-[2-chloro-4-[[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-aminocarbonyl]-5-methoxyphenyl]-2-methoxybenzamide

HRID 345608Notes

Reaction equation

HRID 345608 reaction equation
[OH2:1].[NH2:2][C:3]1[C:30]([Cl:31])=[CH:29][C:6]([C:7]([NH:9][C@H:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:12][C@H:11]2[O:27][CH3:28])=[O:8])=[C:5]([O:32][CH3:33])[CH:4]=1>CO>[NH2:2][C:3]1[C:30]([Cl:31])=[CH:29][C:6]([C:7]([NH:2][C:3]2[CH:4]=[C:5]([O:32][CH3:33])[C:6]([C:7]([NH:9][C@H:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]4[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=4)[CH2:12][C@H:11]3[O:27][CH3:28])=[O:8])=[CH:29][C:30]=2[Cl:31])=[O:1])=[C:5]([O:32][CH3:33])[CH:4]=1

Participants

3

Reactant 1

HCID 13677778Alimix

Product 1

HCID 15096959cis-4-amino-5-chloro-N-[2-chloro-4-[[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-aminocarbonyl]-5-methoxyphenyl]-2-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

40 Parts of cis-4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide monohydrate was boiled in 160 parts of methanol. The product was filtered off while hot and crystallized twice from a mixture of 600 parts of tetrachloromethane and 400 parts of trichloromethane. The product was filtered off, dried and recrystallized from 4-methyl-2-pentanone. The product was filtered off and dried (water-separator) yielding 18.5 parts of cis-4-amino-5-chloro-N-[2-chloro-4-[[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]aminocarbonyl]-5-methoxyphenyl]-2-methoxybenzamide; mp. 181.5° C. (compound 239).

Workup

  1. filtrationThe product was filtered off while hot and
  2. customcrystallized twice from a mixture of 600 parts of tetrachloromethane and 400 parts of trichloromethane
  3. filtrationThe product was filtered off
  4. customdried
  5. customrecrystallized from 4-methyl-2-pentanone
  6. filtrationThe product was filtered off
  7. dry with materialdried (water-separator)

Sources & evidence

ORD record
ord-16ef90a72489480ea319fbc78713b0a4
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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