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

HRID 1739756Notes

Reaction equation

HRID 1739756 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
120 °C

Procedure

Piperazine (23.69 g, 8 mol. equiv.) was melted and 1-(t-butoxycarbonyl)-3-methanesulphonyloxyazetidine (see International Patent Application Publication no. WO93/19059) (8.64 g, 34.4 mmol) added. The mixture was heated at 120° C. for 15 hours under nitrogen. The reaction was cooled to room temperature and the excess piperazine removed under reduced pressure. The residue was then chromatographed on silica gel using gradient elution (methanol:dichloromethane 1:19 changing to 1:4, by volume) to give the title compound (6.32 g). LRMS m/z=242 (m+1)+.

Workup

  1. additionWO93/19059) (8.64 g, 34.4 mmol) added
  2. temperatureThe reaction was cooled to room temperature
  3. customthe excess piperazine removed under reduced pressure
  4. customThe residue was then chromatographed on silica gel using gradient elution (methanol:dichloromethane 1:19 changing to 1:4, by volume)

Sources & evidence

ORD record
ord-be2125c3fdf64f37b224954864abfc98
Source dataset
uspto-grants-1999_10
Patent number
US05968923

Reaction notes

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