rel-(2R,6S)-2,6-dimethylpiperazine → Tert-butyl 3,5-dimethylpiperazine-1-carboxylate

HRID 1437224Notes

Reaction equation

HRID 1437224 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.[C:9]([O:13][C:14](N=C(C1C=CC=CC=1)C#N)=[O:15])([CH3:12])([CH3:11])[CH3:10]>O1CCCC1>[C:9]([O:13][C:14]([N:6]1[CH2:5][CH:4]([CH3:8])[NH:3][CH:2]([CH3:1])[CH2:7]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 53823621HCID 53823621, compound

Product 1

HCID 22219990Tert-butyl 3,5-dimethylpiperazine-1-carboxylateYield 161.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

cis-2,6-Dimethylpiperazine (5.08 g) was added to 2-(tert-butoxycarbonylimino)-2-phenylacetonitrile (11.35 g) in tetrahydrofuran (150 mL) at 0° C., followed by stirring for 2 hours. The reaction solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform−7N ammonia/methanol mixture), to thereby give the title compound (15.36 g, 72%).

Workup

  1. customThe reaction solvent was evaporated under reduced pressure
  2. customThe residue was purified through silica gel column chromatography (chloroform−7N ammonia/methanol mixture)

Sources & evidence

ORD record
ord-d72e34ae435643559d9ddca29db24daa
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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