Sodium Carbonate → (+/-)-3,5-Dimethylphenyl cis-4-[1-[3,5-bis(trifluoromethyl) benzoyl]-2-(phenylmethyl)-4-piperidinyl]-alpha-phenyl-1-piperazineacetate

HRID 1060191Notes

Reaction equation

HRID 1060191 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[CH:37]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:38]([O:40][C:41]1[CH:46]=[C:45]([CH3:47])[CH:44]=[C:43]([CH3:48])[CH:42]=1)=[O:39].C(=O)([O-])[O-].[Na+].[Na+]>CC(CC(C)C)=O>[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]([CH:37]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:38]([O:40][C:41]3[CH:42]=[C:43]([CH3:48])[CH:44]=[C:45]([CH3:47])[CH:46]=3)=[O:39])[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 10340Sodium CarbonateHCID 18630849(+/-)-3,5-Dimethylphenyl alpha-chlorobenzeneacetateHCID 18630855(+/-)-1-[3,5-Bis(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-(1-piperazinyl)piperidine

Product 1

HCID 15513280(+/-)-3,5-Dimethylphenyl cis-4-[1-[3,5-bis(trifluoromethyl) benzoyl]-2-(phenylmethyl)-4-piperidinyl]-alpha-phenyl-1-piperazineacetateYield 43.1%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of compound 15 (2.5 g), intermediate 5 (1.65 g) and sodium carbonate (0.64 g) in methylisobutylketon (50 ml) was stirred and refluxed for 3 hours. The reaction mixture was washed and the separated organic layer was dried, filtered and the solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2/CH3OH 100/0 and 99.5/0.5). The pure fractions were collected and the solvent was evaporated, yielding 1.59 g (43%) of (±)-3,5-dimethylphenyl cis-4-[1-[3,5-bis(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-piperidinyl]-α-phenyl-1-piperazineacetate (compound 43; mp. 88.1° C.).

Workup

  1. temperaturerefluxed for 3 hours
  2. washThe reaction mixture was washed
  3. customthe separated organic layer was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified over silica gel on a glass
  7. filtrationfilter (eluent: CH2Cl2/CH3OH 100/0 and 99.5/0.5)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a43de800e945445f978495c9b2a5f7a5
Source dataset
uspto-grants-2003_02
Patent number
US06521621B1

Reaction notes

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