Hydrochloric Acid → HCID 68694707, compound

HRID 1990975Notes

Reaction equation

HRID 1990975 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][CH:20]=[C:19]3[S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:34]C(OC(Cl)=O)C.Cl.C(OCC)C>ClCCCl>[ClH:34].[C:28]1([S:25]([C:19]2[C:18]3[C:22](=[CH:23][CH:24]=[C:16]([CH2:15][CH2:14][N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:17]=3)[NH:21][CH:20]=2)(=[O:26])=[O:27])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 5213051-Chloroethyl chloroformateHCID 58955121HCID 58955121, compound

Product 1

HCID 68694707HCID 68694707, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A stirred mixture of 5-[2-(4-benzylpiperazin-1-yl)ethyl]-3-(phenylsulfonyl)-1H-indole (0.110 g, 0.24 mmol) and 1-chloroethylchloroformate (0.05 mL, 0.36 mmlole) in 1,2-dichloroethane (2 mL) was heated to reflux for 12 hours. The reaction mixture was cooled and concentrated in vacuo to a brown glass. The glass was taken up in methanol (4 mL) and heated to reflux for 6 h, then cooled and concentrated in vacuo to a semi solid. This solid was dissolved in diethyl ether and treated with 1 N HCl in diethyl ether (0.22 mL, 0.22 mmol) to afford a white precipitate isolated by vacuum filtration. Mp: 220° C. MS (ES+): 370 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo to a brown glass
  5. temperatureheated
  6. temperatureto reflux for 6 h
  7. temperaturecooled
  8. concentrationconcentrated in vacuo to a semi solid
  9. dissolutionThis solid was dissolved in diethyl ether
  10. customto afford a white precipitate
  11. customisolated by vacuum filtration

Sources & evidence

ORD record
ord-06e3e8bde20e4df68b5a2eac8a6049a4
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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