4-Fluoroaniline → HCID 46851969, compound

HRID 1951506Notes

Reaction equation

HRID 1951506 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])(=[O:4])=[O:3].[N:14]1([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+].[F:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1>ClCCl.CO>[F:31][C:32]1[CH:38]=[CH:37][C:35]([NH:36][S:2]([C:5]2[CH:13]=[CH:12][CH:11]=[C:7]([C:8]([N:22]3[CH2:23][CH2:24][CH:19]([N:14]4[CH2:18][CH2:17][CH2:16][CH2:15]4)[CH2:20][CH2:21]3)=[O:9])[CH:6]=2)(=[O:4])=[O:3])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 97314-FluoroanilineHCID 10340Sodium CarbonateHCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 787034-(1-Pyrrolidinyl)piperidine

Product 1

HCID 46851969HCID 46851969, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 3-(chlorosulfonyl)benzoyl chloride (0.178 g, 0.746 mmol) in anhydrous dichloromethane (10 mL) was added 4-(pyrrolidin-1-yl)piperidine (0.115 g, 0.746 mmol) in dichloromethane (4 mL) slowly over 10 minutes at room temperature. Then sodium carbonate (0.277 g, 2.61 mmol) was added. The mixture was stirred at room temperature for 5 hours. Then 4-fluoroaniline (0.83 g, 7.5 mmol) was added. The mixture was stirred at room temperature overnight. Then methanol (5 mL) was added, the mixture was stirred for 20 minutes, then filtered, and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate, then methanol/ethyl acetate=1:10) to give the titled compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37 (m, 2H), 1.73 (m, 6H), 1.93 (m, 2H), 2.63 (m, 4H), 2.96 (m, 2H), 4.25 (m, 1H), 7.08 (m, 4H), 7.62 (m, 3H), 7.79 (m, 1H); MS (ESI) m/z 432 (M+H)+.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. stirringthe mixture was stirred for 20 minutes
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-dfb7e2ed379d4413b1f2a5accfa818f6
Source dataset
uspto-grants-2013_03
Patent number
US08404719B2

Reaction notes

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