Piperazine → HCID 14988910, compound

HRID 964366Notes

Reaction equation

HRID 964366 reaction equation
[OH:1][CH:2]1[CH2:9][CH2:8][C:5]2([O:7][CH2:6]2)[CH:4]([C:10]2([CH3:18])[CH:12]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[O:11]2)[CH:3]1[O:19][CH3:20].Cl[C:22](OC1C=CC([N+]([O-])=O)=CC=1)=[O:23].[NH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.[CH2:40]([S:42](Cl)(=[O:44])=[O:43])[CH3:41]>ClCCl.C(OCC)C.N1C=CC=CC=1>[CH2:40]([S:42]([N:34]1[CH2:39][CH2:38][N:37]([C:22]([O:1][CH:2]2[CH2:9][CH2:8][C:5]3([O:7][CH2:6]3)[CH:4]([C:10]3([CH3:18])[CH:12]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[O:11]3)[CH:3]2[O:19][CH3:20])=[O:23])[CH2:36][CH2:35]1)(=[O:44])=[O:43])[CH3:41]

Participants

8

Reactant 4

HCID 4837PiperazineHCID 11667Ethanesulfonyl chlorideHCID 821294-Nitrophenyl chloroformateHCID 2190894-(1,5-Dimethyl-1,2-epoxy-4-hexenyl)-5-methoxy-1-oxaspiro(2.5)octan-6-ol

Product 1

HCID 14988910HCID 14988910, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-hydroxy-5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2,5]octane (400 mg), p-nitrophenyl chloroformate (570 mg) and pyridine (1.37 ml) in dichloromethane (6 ml) was stirred for 3 hours at ambient temperature and then piperazine (1.0 g) was added thereto. After stirring at ambient temperature for half an hour, the mixture was treated with ethanesulfonyl chloride (183 mg). The reaction mixture was stirred for 15 minutes at 0° C. and for 3 hours at ambient temperature. The resulting mixture was diluted with diethyl ether and washed with 1N HCl, 1N NaOH and brine. The organic layer was dried and concentrated in vacuo to give a crude oil which was purified by silica gel column chromatography to yield 6-[4-(ethanesulfonyl)piperazin-1-ylcarbonyloxy]-5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2,5]octane as crystal.

Workup

  1. stirringAfter stirring at ambient temperature for half an hour
  2. stirringThe reaction mixture was stirred for 15 minutes at 0° C. and for 3 hours at ambient temperature
  3. washwashed with 1N HCl, 1N NaOH and brine
  4. customThe organic layer was dried
  5. concentrationconcentrated in vacuo
  6. customto give a crude oil which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff9c7b5aba7f43e6b7f9bb32b14db366
Source dataset
uspto-grants-1998_06
Patent number
US05767293

Reaction notes

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