HCID 86757040, compound → HCID 86757039, compound

HRID 1068662Notes

Reaction equation

HRID 1068662 reaction equation
[F:1][C:2]([F:51])([F:50])[C:3]1[CH:4]=[C:5]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[CH2:19][CH2:18][C:17](=[C:20]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[CH2:24][CH2:23][N:22]4[C:31]([CH2:34][OH:35])=[CH:32][N:33]=[C:21]34)[CH2:16][CH2:15]2)[CH2:10][C@@H:9]1[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:7]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:49][C:46]([F:47])([F:48])[C:44]1[CH:43]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:51])[F:50])[CH:45]=1)[C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[CH2:19][CH2:18][C:17](=[C:20]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[CH2:24][CH2:23][N:22]4[C:31]([CH:34]=[O:35])=[CH:32][N:33]=[C:21]34)[CH2:16][CH2:15]2)[CH2:10][C@@H:9]1[CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:7]

Participants

4

Reactant 1

HCID 86757040HCID 86757040, compound

Product 1

HCID 86757039HCID 86757039, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of (±)-cis-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-[5,6-dihydro-3-(hydroxymethyl)-11H-imidazo[2,1-b][3]benzazepin-11-ylidene]-1-piperidinyl]-2-(phenylmethyl)piperidine (4.5 g) and manganese dioxide (20 g) in CHCl3 (200 ml) was stirred and refluxed for 1 hour. The mixture was filtered warm over dicalite and the filtrate was evaporated. The residue as purified over silica gel on a glass filter (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was purified by HPLC (eluent: CH2Cl2/CH3OH 100/0 to 95/5). The pure fractions were collected and the solvent was evaporated, yielding 3.1 g (70%) of (±)-cis-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-(3-formyl-5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-piperidinyl]-2-(phenylmethyl)piperidine (comp. 11; mp. 125.8° C.).

Workup

  1. temperaturerefluxed for 1 hour
  2. filtrationThe mixture was filtered
  3. temperaturewarm over dicalite
  4. customthe filtrate was evaporated
  5. customThe residue as purified over silica gel on a glass
  6. filtrationfilter (eluent: CH2Cl2/CH3OH 95/5)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue was purified by HPLC (eluent: CH2Cl2/CH3OH 100/0 to 95/5)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a3f2d04f3af947948bfb81fba78eb71b
Source dataset
uspto-grants-2001_06
Patent number
US06251894B1

Reaction notes

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