Hydrochloric Acid → HCID 14230187, compound

HRID 35347Notes

Reaction equation

HRID 35347 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([NH:21][C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])=[O:20])[CH2:14][CH:13]2[C:30]([O:32]CC)=[O:31])=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+]>CC(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([NH:21][C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])=[O:20])[CH2:14][CH:13]2[C:30]([OH:32])=[O:31])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21295667HCID 21295667, compound

Product 1

HCID 14230187HCID 14230187, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3.3 parts of ethyl 1-[4,4-bis(4-fluorophenyl)butyl]-4-[2-[(2,6-dichlorophenyl)amino]-2-oxoethyl]-2-piperazinecarboxylate and 60 parts of a hydrochloric acid solution 12N was stirred for 8 hours at 100° C. in an oil-bath. 2-Propanone was added whereupon a solution was obtained. The pH was adjusted to 5 with sodium hydrogen carbonate and the 2-propanone was evaporated: a sticky oil in water was remained. The aqueous phase was decanted and the sticky oil was taken up in 24 parts of 4-methyl-2-pentanone while warming. The solid product was filtered off and boiled in 120 parts of acetonitrile. After cooling for a while, the less pure product was filtered off and the filtrate was cooled. The product was filtered off and dried, yielding 0.31 parts of 1-[4,4-bis(4-fluorophenyl)butyl]-4-[2-[(2,6-dichlorophenyl)amino]-2-oxoethyl]-2-piperazinecarboxylic acid; mp. 204.3° C. (compound 172).

Workup

  1. customwas obtained
  2. customthe 2-propanone was evaporated
  3. customThe aqueous phase was decanted
  4. temperaturewhile warming
  5. filtrationThe solid product was filtered off
  6. temperatureAfter cooling for a while
  7. filtrationthe less pure product was filtered off
  8. temperaturethe filtrate was cooled
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-86dfa8485e1744c3a86045805f5e63d8
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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