2,3-Dihydrospiro(indene-1,4'-piperidine) → HCID 54163594, compound

HRID 2288189Notes

Reaction equation

HRID 2288189 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16]OS(C)(=O)=O)[CH2:10][C@H:9]1[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:7].[NH:41]1[CH2:46][CH2:45][C:44]2([C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[CH2:48][CH2:47]2)[CH2:43][CH2:42]1>C(#N)C>[F:36][C:35]([F:38])([F:37])[C:33]1[CH:32]=[C:5]([CH:4]=[C:3]([C:2]([F:39])([F:1])[F:40])[CH:34]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:41]2[CH2:46][CH2:45][C:44]3([C:54]4[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=4)[CH2:48][CH2:47]3)[CH2:43][CH2:42]2)[CH2:10][C@H:9]1[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:7]

Participants

4

Reactant 2

HCID 156376162,3-Dihydrospiro(indene-1,4'-piperidine)HCID 53774435HCID 53774435, compound

Product 1

HCID 54163594HCID 54163594, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(3-methylsulfonyloxypropyl)piperazine (200 mg) and spiro[indan-1,4'-piperidine] (70 mg) in acetonitrile (3 ml) was refluxed for 1.5 hours. The reaction mixture was evaporated under reduced pressure and then the residue was purified by column chromatography on silica gel using dichloromethane-methanol (10:1) as an eluent to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[3-(spiro[indan-1,4'-piperidine]-1'-yl)propyl]-2-(1H-indol-3-ylmethyl)piperazine (208 mg) as a powder.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b9b93374bfab4defa1c49ba7bd35381f
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

Loading…