Potassium Carbonate → HCID 67207709, compound

HRID 1894356Notes

Reaction equation

HRID 1894356 reaction equation
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13]2)(=O)=O)=CC=1.[CH2:20]([O:27][C:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)C.O>[CH2:20]([O:27][C:28]([N:30]1[CH2:35][CH2:34][N:33]([CH2:11][C@H:12]2[CH2:16][O:15][C:14]([CH3:17])([CH3:18])[O:13]2)[CH2:32][CH2:31]1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 643495Benzyl piperazine-1-carboxylateHCID 2723760(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate

Product 1

HCID 67207709HCID 67207709, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
127 °C

Procedure

(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate (286 mg, 1.0 mmol, Aldrich) and piperazine-1-carboxylic acid benzyl ester (235 mg, 1.1 mmol, Aldrich) were combined with potassium carbonate (148 g, 1.1 mmol) in dry toluene (6 mL) in a 10 mL pressure vessel. This was well stirred and heated to 127° C. for 20 h. The reaction was cooled, diluted with ethyl ether (20 mL) and 20 mL of water. The organics were washed with water, brine, dried (MgSO4) and evaporated to give 4-(S)-(−)-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-piperazine-1-carboxylic acid benzyl ester as a heavy oil which was purified by flash column chromatography (silica gel, eluting with 3% triethylamine and 1:1 ethyl acetate:hexane to ethyl acetate). LR-MS: 334 [(M+H)+].4-(S)-(−)-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-piperazine-1-carboxylic acid benzyl ester (220 mg, 0.65 mmol) was dissolved in 20 mL of ethanol and 10% palladium on carbon (50 mg, Aldrich). The mixture was hydrogenated in a Parr reactor at 40 psi for 18 h. The reaction mixture was filtered through Celite and evaporated to give an oil. The oil was mostly dissolved in hexane, treated with Norite, filtered and crystallized from cold hexane to give 1-(S)-(−)-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-piperazine. LR-MS: 200 [(M+H)+].

Workup

  1. temperatureThe reaction was cooled
  2. washThe organics were washed with water, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-3042a3dae5e644f4bb0f0ef3c49b17c6
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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