Piperidine → HCID 67005741, compound

HRID 563143Notes

Reaction equation

HRID 563143 reaction equation
C1C2C(COC([N:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:60])[C@@H:25]([N:33]([CH2:48][C:49]4[CH:54]=[CH:53][C:52]([CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])=[CH:51][CH:50]=4)[C:34](=[O:47])[CH:35]=[CH:36][C:37]4[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=4)[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:20][CH2:19]3)=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1.CCOC(C)=O>CN(C=O)C>[CH2:26]([C@H:25]([N:33]([CH2:48][C:49]1[CH:50]=[CH:51][C:52]([CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])=[CH:53][CH:54]=1)[C:34](=[O:47])[CH:35]=[CH:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=1)[C:24](=[O:60])[N:21]1[CH2:20][CH2:19][NH:18][CH2:23][CH2:22]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 67005749HCID 67005749, compound

Product 1

HCID 67005741HCID 67005741, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-{(4-pentyl-benzyl)-[3-(4-trifluoromethyl-phenyl)-acryloyl]-amino}-(S)-3-phenyl-propionyl)-piperazine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (1.75 g, 2.15 mmol) was dissolved in DMF (47.5 mL) and piperidine (2.5 mL) was added. Stirring was continued at rt for 30 min. EtOAc (150 mL) was added and the mixture was washed with water (2×150 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (silicagel, MeOH/DCM=1/99) to give 1.05 g (82.5%) of N—((S)-1-Benzyl-2-oxo-2-piperazin-1-yl-ethyl)-N-(4-pentyl-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide. LC-MS: tR=0.97 min; [M+H]+=592.19.

Workup

  1. washthe mixture was washed with water (2×150 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silicagel, MeOH/DCM=1/99)

Sources & evidence

ORD record
ord-a8891680537e47d9817ce0baa7ca7644
Source dataset
uspto-grants-2011_11
Patent number
US08067419B2

Reaction notes

Loading…