Phenethyl bromide → HCID 10618874, compound

HRID 2202152Notes

Reaction equation

HRID 2202152 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:15][CH2:14]3)[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 4491264-[3-(4-Chlorophenyl)-1H-pyrazol-5-yl]piperidine2×

Product 1

HCID 10618874HCID 10618874, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[3-(4-chlorophenyl)-1H-pyrazol-5-yl]piperidine (INTERMEDIATE 7, 4 g, 15.28 mmol) in 60 mL DMF was added K2CO3 (63 g, 45.8 mmol), and 2-(bromoethyl)benzene (2.3 mL, 16.8 mmol). The reaction mixture was stirred at ambient temperature overnight, diluted with EtOAc, and washed three times with water. The organic layer was separated, dried (MgSO4), and concentrated under reduced pressure. LC-MS m/z=366.17 [M+1]+.

Workup

  1. washwashed three times with water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1611d3c8b3a147a3a4cc38eadca9dfc5
Source dataset
uspto-grants-2016_06
Patent number
US09365539B2

Reaction notes

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