Piperazine → HCID 86752430, compound

HRID 1739753Notes

Reaction equation

HRID 1739753 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]([O:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>>[CH3:22][S:19]([OH:21])(=[O:20])=[O:18].[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 86752430HCID 86752430, compound

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). LRMS m/z=242 (m+1)+.

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-a7f235e886284bae8b0efafe1b3a2416
Source dataset
uspto-grants-1999_10
Patent number
US05968923

Reaction notes

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