Piperidine → HCID 51892131, compound

HRID 2366833Notes

Reaction equation

HRID 2366833 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8]Cl)[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(#N)C.CO.O>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:6]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 518920744-Bromo-1-(2-chloroethyl)-1H-pyrazole

Product 1

HCID 51892131HCID 51892131, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

4-bromo-1-(2-chloroethyl)-1H-pyrazole (see Intermediate 29 for a preparation) (120 mg, 0.573 mmol), potassium carbonate (158 mg, 1.146 mmol) and Piperidine (0.113 mL, 1.146 mmol) was stirred in Acetonitrile (2 mL) and heated to 60° C. for five days. The mixture was fully dissolved in MeOH/water and loaded on to a 10 g SCX cartridge. The SCX cartridge was eluted with MeOH (100 ml), followed by 2M methanolic ammonia (50 ml). The basic fractions were evaporated to dryness to give the desired product (101 mg). LCMS (Method A): Rt=1.04, MH+=260

Workup

  1. washThe SCX cartridge was eluted with MeOH (100 ml)
  2. customThe basic fractions were evaporated to dryness

Sources & evidence

ORD record
ord-37ab5729ae2d4df7bc3946d43b81883f
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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