Piperazine → tert-Butyl 3-(piperazin-1-yl)azetidine-1-carboxylate

HRID 1066066Notes

Reaction equation

HRID 1066066 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7]([O:11][C:12]([N:14]1[CH2:17][CH:16](OS(C)(=O)=O)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>>[C:7]([O:11][C:12]([N:14]1[CH2:17][CH:16]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

3

Reactant 2

HCID 4837PiperazineHCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

Product 1

HCID 19360775tert-Butyl 3-(piperazin-1-yl)azetidine-1-carboxylate

Conditions

Temperature
115 °C

Procedure

Piperazine (149.2 g, 8 mol. equiv.) was heated to a melt and 1-(t-butoxycarbonyl)-3-methanesulphonyloxy-azetidine (see International Patent Application Publication no. WO93/19059) (54.5 g, 217 mmol) was then added. The mixture was heated at 115° C. for twenty four hours. The reaction was cooled and the excess piperazine removed under reduced pressure. The residue was purified by flash column chromatography on silica gel using methanol:dichloromethane (5:95, by volume) as the eluant to give the title compound (51 g).

Workup

  1. additionWO93/19059) (54.5 g, 217 mmol) was then added
  2. temperatureThe reaction was cooled
  3. customthe excess piperazine removed under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-01c6da9e6f9d44bba581b10f88466286
Source dataset
uspto-grants-2001_06
Patent number
US06242438B1

Reaction notes

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