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Triethylamine → 3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

HRID 2267491
Notes
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Reaction equation

HRID 2267491 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=2)[NH:12][CH:11]=[C:10]3[CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:32][CH2:33][CH2:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[Cl:32][CH2:33][CH2:34][S:35]([N:22]1[CH2:23][CH2:24][CH:19]([C:10]2[C:9]3[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:8]=3)[NH:12][CH:11]=2)[CH2:20][CH2:21]1)(=[O:37])=[O:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 114271625-Phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide

Product 1

HCID 590033063-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamideYield 32%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide (65 mg, 0.2 mmol) in CH2Cl2 (5 mL) at 0° C., triethylamine (0.11 mL, 0.8 mmol) and 2-chloroethanesulfonyl chloride (0.042 mL, 0.4 mmol) were added. After stirring at 0° C. for 30 min. the reaction mixture was partitioned between CH2Cl2 and water. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×). The combined organic phase was dried over magnesium sulfate and the solvent removed under reduced pressure. The resulting residue was purified by filtration through an SPE Cartridge (Aminopropyl NH2, 500 mg/6 mL) to give the desired product (26 mg, 32%).

Workup

  1. customwas partitioned between CH2Cl2 and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  4. dry with materialThe combined organic phase was dried over magnesium sulfate
  5. customthe solvent removed under reduced pressure
  6. filtrationThe resulting residue was purified by filtration through an SPE Cartridge (Aminopropyl NH2, 500 mg/6 mL)

Sources & evidence

ORD record
ord-ea224ef05d6e49f5a75e75a0684f76a7
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858796B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes