Diisopropylethylamine → 3-Phenylsulfonyl-8-piperazin-1-yl-quinoline hydrochloride

HRID 2116530Notes

Reaction equation

HRID 2116530 reaction equation
Cl.C[N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][C:15]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:14]3)[CH2:5][CH2:4]1.[Cl:28]C(OC(Cl)C)=O.C(N(CC)C(C)C)(C)C>ClCCCl>[ClH:28].[C:22]1([S:19]([C:15]2[CH:16]=[N:17][C:18]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][C:9]=3[N:6]2[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]2)(=[O:21])=[O:20])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 69198975HCID 69198975, compound

Product 1

HCID 569721413-Phenylsulfonyl-8-piperazin-1-yl-quinoline hydrochlorideYield 52.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A stirred solution of 8-(4-methyl-piperazin-1-yl)-3-phenylsulfonylquinoline hydrochloride (D10) (0.148 g, 0.4 mmol), 1-chloroethyl chloroformate (0.093 ml, 0.85 mmol) and N,N-diisopropylethylamine (0.148 ml, 0.85 mmol) in 1,2-dichloroethane (9 ml) was heated at reflux for 1.25 h under argon. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to an oil. The oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane, pooling fractions which contained the major component (Rf 0.9, methanol/dichloromethane 1:19). The purified material was redissolved in methanol (15 ml) and the solution was refluxed for 1 h under argon. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to a solid which was stirred with diethyl ether (5 ml) and filtered to afford the title compound (D11) (0.08 g, 0.21 mmol, 51%);

Workup

  1. temperatureat reflux for 1.25 h under argon
  2. concentrationconcentrated in vacuo to an oil
  3. customThe oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane, pooling fractions which
  4. dissolutionThe purified material was redissolved in methanol (15 ml)
  5. temperaturethe solution was refluxed for 1 h under argon
  6. temperatureThe reaction mixture was cooled to ambient temperature
  7. concentrationconcentrated in vacuo to a solid which
  8. filtrationfiltered

Sources & evidence

ORD record
ord-1ea7b831b4ce4031b4a47fb6fc36be36
Source dataset
uspto-grants-2008_10
Patent number
US07439244B2

Reaction notes

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