Triethylamine → HCID 86744880, compound

HRID 1494654Notes

Reaction equation

HRID 1494654 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH:15]([CH3:19])[CH2:14]2)=[CH:4][CH:3]=1.[C:27]([C:30]1[CH:35]=[C:34]([Cl:36])[C:33]([NH:37][C:38](=[O:41])[CH2:39]Cl)=[C:32]([Cl:42])[CH:31]=1)(=[O:29])[CH3:28].C(N(CC)CC)C>CN(C)C=O>[ClH:36].[ClH:36].[C:27]([C:30]1[CH:31]=[C:32]([Cl:42])[C:33]([NH:37][C:38](=[O:41])[CH2:39][N:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[CH2:14][CH:15]2[CH3:19])=[C:34]([Cl:36])[CH:35]=1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15087730HCID 15087730, compoundHCID 15087743HCID 15087743, compound

Product 1

HCID 86744880HCID 86744880, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.6 parts of 1-[5,5-bis(4-fluorophenyl)pentyl]-3-methylpiperazine, 3 parts of N-(4-acetyl-2,6-dichlorophenyl)-2-chloroacetamide, 1.9 parts of N,N-diethylethanamine and 45 parts of N,N-dimethyformamide was stirred for 20 hours at 70° C. The reaction mixture was evaporated and the residue was taken up in a mixture of sodium carbonate and water. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol and 2,2'-oxybispropane. The product was filtered off and dried in vacuo at 40° C., yielding 1.74 parts (22.8%) of N-(4-acetyl-2,6-dichlorophenyl)-4-[5,5-bis(4-fluoro-phenyl)pentyl]-2-methyl-1-piperazineacetamide dihydrochloride, 2-propanol(1:1), sesquihydrate; mp. 176.3° C. (compound 54).

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was taken up in a mixture of sodium carbonate and water
  3. extractionThe product was extracted with dichloromethane
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. filtrationThe product was filtered off
  13. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-b364a1271dbb4f0eba072385fd3ba8ab
Source dataset
uspto-grants-1991_06
Patent number
US05026853

Reaction notes

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