1,2,3,4-Tetrahydroisoquinoline → HCID 54384023, compound

HRID 2288187Notes

Reaction equation

HRID 2288187 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].[CH2:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:44][CH2:43][NH:42]1>CO>[F:39][C:2]([F:40])([F:1])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:34]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:42]2[CH2:43][CH2:44][C:45]3[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:41]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 70461,2,3,4-TetrahydroisoquinolineHCID 53774435HCID 53774435, compound

Product 1

HCID 54384023HCID 54384023, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(3-methylsulfonyloxypropyl) piperazine (200 mg) and 1,2,3,4-tetrahydroisoquinoline (90 mg) in methanol (3 ml) was stirred for 1.5 hours at reflux temperature. The reaction mixture was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using ethyl acetate-methanol (10:1) as an eluent to give (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(1H-indol-3-ylmethyl)-4-[3-[1,2,3,4-tetrahydroisoquinolin-2-yl]propyl]piperazine (167 mg) as a powder.

Workup

  1. temperatureat reflux temperature
  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-6f9950e31c1246c5b10967666434ac55
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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