Sodium Bicarbonate → HCID 86756486, compound

HRID 1530929Notes

Reaction equation

HRID 1530929 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:10][CH:9]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:7].[Cl:36][C:37]1[CH:38]=[C:39]([CH:44]([CH2:56][CH2:57]OS(C)(=O)=O)[CH2:45][N:46]([CH3:55])[C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:40]=[CH:41][C:42]=1[Cl:43].[C:63]([O-:66])([OH:65])=O.[Na+]>C(O)C>[C:6]([OH:54])(=[O:7])/[CH:5]=[CH:27]/[C:63]([OH:66])=[O:65].[F:35][C:2]([F:34])([F:1])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:29]=1)[C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[CH2:15][CH2:16][N:17]([CH2:57][CH2:56][CH:44]([C:39]3[CH:40]=[CH:41][C:42]([Cl:43])=[C:37]([Cl:36])[CH:38]=3)[CH2:45][N:46]([CH3:55])[C:47](=[O:54])[C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[CH2:18][CH2:19]2)[CH2:10][C@@H:9]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:7]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18630855(+/-)-1-[3,5-Bis(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-(1-piperazinyl)piperidineHCID 18630858HCID 18630858, compound

Product 1

HCID 86756486HCID 86756486, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 15 (0.005 mol), N-[2-(3,4-dichlorophenyl)-4-[(methylsulfonyl)oxy]butyl]-N-methyl benzamide (0.0055 mol) and NaHCO3 (0.0055 mol) in ethanol (50 ml) was stirred and refluxed for 6 hours. The solvent was evaporated, the residue was taken up in water and extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2/CH3OH 100/0, 99/1, 98/2 and 97/3). The pure fractions were collected and the solvent was evaporated. The residue was converted into the fumaric acid salt (1:2) with ethanol. The precipitate was filtered off and dried, yielding 1.42 g (27%) of (±)-cis-N-[4-[4-[1-[3,5-bis(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-piperidinyl]-1-piperazinyl]-2-(3,4-dichlorophenyl)butyl]-N-methylbenzamide (E)-2-butenedioate (1:2) (compound 93).

Workup

  1. temperaturerefluxed for 6 hours
  2. customThe solvent was evaporated
  3. extractionextracted with CH2Cl2
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified over silica gel on a glass
  9. filtrationfilter (eluent: CH2Cl2/CH3OH 100/0, 99/1, 98/2 and 97/3)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-8d78ee939abb44568b8f1960189f6b7b
Source dataset
uspto-grants-2001_03
Patent number
US06197772B1

Reaction notes

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