Chlorosuccinimide → HCID 86590505, compound

HRID 1760632Notes

Reaction equation

HRID 1760632 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([C@H:12]3[CH2:17][CH2:16][NH:15][C@@H:14]([CH3:18])[CH2:13]3)[S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.C1C(=O)N([Cl:26])C(=O)C1>C1COCC1>[Cl:26][N:15]1[CH2:16][CH2:17][C@H:12]([C:9]2[S:8][C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=3[CH:10]=2)[CH2:13][C@@H:14]1[CH3:18]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 69738662HCID 69738662, compound

Product 1

HCID 86590505HCID 86590505, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cis-(±)-4-(4-methoxybenzo[b]thiophen-2-yl)-2-methylpiperidine in THF (35 mL) was cooled to 0° C. (ice-water bath), then treated with NCS (2.26 g, 16.94 mol). After stirring 15 minutes, the ice-water bath was removed and the mixture was stirred at room temperature for 45 minutes. The mixture was then concentrated under reduced pressure and diluted with Et2O (100 mL), saturated aqueous NaHCO3 (50 mL) and H2O (50 mL). The mixture was shaken and partitioned in a separatory funnel. The aqueous layer was separated and extracted once with Et2O. The combined organic layers were washed once with H2O (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give the cis-(±)-N-chloro-4-(4-methoxybenzo[b]thiophen-2-yl)-2-methylpiperidine as a yellow oil (4.78 g, 99%).

Workup

  1. customthe ice-water bath was removed
  2. stirringthe mixture was stirred at room temperature for 45 minutes
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. additiondiluted with Et2O (100 mL), saturated aqueous NaHCO3 (50 mL) and H2O (50 mL)
  5. stirringThe mixture was shaken
  6. custompartitioned in a separatory funnel
  7. customThe aqueous layer was separated
  8. extractionextracted once with Et2O
  9. washThe combined organic layers were washed once with H2O (50 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa41189fc7b643d392f688bbdab0d83d
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

Loading…