Piperazine → HCID 86752430, compound

HRID 377029Notes

Reaction equation

HRID 377029 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-methanesulphonyloxyazetidine (see (International Patent Application Publication No. WO93/19059) (54.5 g, 217 mmol) was then added. The mixture was heated at 115° C. for 24 hours, then cooled and the excess piperazine removed in vacuo. The residue was purified by flash chromatography (silica, methanol:dichloromethane, 1:19) to give the title compound (51 g).

Workup

  1. additionWO93/19059) (54.5 g, 217 mmol) was then added
  2. temperaturecooled
  3. customthe excess piperazine removed in vacuo
  4. customThe residue was purified by flash chromatography (silica, methanol:dichloromethane, 1:19)

Sources & evidence

ORD record
ord-e78f43022a064485b6f9a8235c3cb52d
Source dataset
uspto-grants-2000_02
Patent number
US06022971

Reaction notes

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