Potassium Carbonate → HCID 68864592, compound

HRID 1986622Notes

Reaction equation

HRID 1986622 reaction equation
[CH2:1]([N:4]1[CH2:9][C@@H:8]([CH3:10])[NH:7][CH2:6][C@@H:5]1[CH3:11])[CH:2]=[CH2:3].[Cl:12][CH2:13][CH2:14][CH2:15]I.[C:17]([O-])([O-])=[O:18].[K+].[K+]>CC(C)=O>[NH3:4].[CH3:17][OH:18].[CH2:1]([N:4]1[CH2:9][C@@H:8]([CH3:10])[N:7]([CH2:15][CH2:14][CH2:13][Cl:12])[CH2:6][C@@H:5]1[CH3:11])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 813631-Chloro-3-iodopropaneHCID 11291191(2S,5R)-1-allyl-2,5-dimethylpiperazine

Product 2

HCID 21705897Ammonia methanolHCID 68864592HCID 68864592, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (+)-(2S,5R)-1-allyl-2,5-dimethylpiperazine (10.6 g, 68.7 mmol, prepared according to the literature procedure described by Janetka, J. W. et al., J. Org. Chem., 2003, 68, 3976-3980), 1-chloro-3-iodo-propane (16.9 g, 82.8 mmol, 1.2 eq), and K2CO3 (24.6 g, 178 mmol, 2.6 eq) in acetone (230 mL) was heated at 50° C. for 16 hours. The mixture was cooled to room temperature, filtered through Celite, and the filtrate was concentrated in vacuo. Chromatography on silica gel using a gradient of 2M NH3/MeOH in CH2Cl2 (0-2%) gave 14.05 g (89%) of (2S,5R)-1-allyl-4-(3-chloro-propyl)-2,5-dimethyl-piperazine as a light yellow oil.

Workup

  1. customprepared
  2. filtrationfiltered through Celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fa081b0a200c45ce88292f5efb1d1202
Source dataset
uspto-grants-2009_06
Patent number
US07550467B2

Reaction notes

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