Ethanol → HCID 22250319, compound

HRID 733043Notes

Reaction equation

HRID 733043 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])=[CH:15]2)[CH2:9]1)C1C=CC=CC=1.[Cl:32]C(OC(Cl)C)=O.C(O)C.CCOCC>ClCCCl>[ClH:32].[C:26]1([S:23]([C:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]([CH:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)[CH:15]=2)(=[O:24])=[O:25])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 5213051-Chloroethyl chloroformateHCID 102521303-(benzenesulfonyl)-1-(1-benzylpiperidin-3-yl)indole

Product 1

HCID 22250319HCID 22250319, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1-(1-benzylpiperidin-3-yl)-3-(phenylsulfonyl)-1H-indole (431 mg, 1.00 mmol) in dry 1,2-dichloroethane is treated with 1-chloroethyl chloroformate (0.27 mL, 2.50 mmol), heated at reflux temperature for 2.5 h, cooled and concentrated in vacuo (reconcentrated twice from CH2Cl2). The resulting residue is heated at reflux temperature in methanol for 3 h, cooled and concentrated in vacuo to give an oil. The oil is reconcentrated from ethanol and then from ether to give a tan solid. The solid is triturated with ethanol and filtered. The filtercake is dried under vacuum to afford the title product as an off-white solid, 322 mg (85% yield), mp 254-256° C., identified by HNMR and mass spectral analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2.5 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo (
  5. temperatureThe resulting residue is heated
  6. temperatureat reflux temperature in methanol for 3 h
  7. temperaturecooled
  8. concentrationconcentrated in vacuo
  9. customto give an oil
  10. customThe solid is triturated with ethanol
  11. filtrationfiltered
  12. customThe filtercake is dried under vacuum

Sources & evidence

ORD record
ord-1610a33c6a64416887a0fc797c208783
Source dataset
uspto-grants-2009_09
Patent number
US07589108B2

Reaction notes

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