Potassium Carbonate → HCID 11121342, compound

HRID 1457808Notes

Reaction equation

HRID 1457808 reaction equation
Cl.[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CN(C=O)C>[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]1[CH2:12][CH2:13][N:14]([CH2:28][C:27]2[CH:30]=[CH:31][C:24]([Cl:23])=[CH:25][CH:26]=2)[CH2:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 22100972HCID 22100972, compound

Product 1

HCID 11121342HCID 11121342, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(Benzothiophen-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (250 mg, 0.99 mmol) was dissolved in DMF (5 ml), potassium carbonate (412 mg, 2.9 mmol) added, and the reaction mixture stirred at room temperature for 10 minutes. 4-Chlorobenzyl bromide (306 mg, 1.5 mmol) was added and the resulting reaction mixture stirred at room temperature overnight. After dilution with water (50 ml), the product was extracted into ethyl acetate (3×40 ml). The combined organic layers were washed with brine (100 ml), dried (MgSO4) and concentrated. The crude product was triturated with methanol to yield a pale brown solid. Recrystallisation from hot dichloromethane and methanol gave the title compound as a pale yellow solid (60 mg, 18%); (Found: C, 70.33; H, 5.20; N, 4.16. C20H18 ClNS requires C, 70.68; H, 5.34; N, 4.12%); δH (CDCl3), 2.64 (2H, m, NCH2CH2), 2.72 (2H, m, NCH2CH2), 3.18 (2H, m, NCH2CH2), 3.61 (2H, s, NCH2Ar), 6.18 (1H, m, NCH2CH2), 7.12 (1H, s, ArH), 7.28 (6H, m, ArH), 7.66 (1H, d of d, J 6Hz, J 2Hz, ArH), 7.74 (1H, d of d, J 6.7Hz, J 2Hz, ArH). m/z (ES+) 340 (M+1)+.

Workup

  1. customthe resulting reaction mixture
  2. stirringstirred at room temperature overnight
  3. extractionAfter dilution with water (50 ml), the product was extracted into ethyl acetate (3×40 ml)
  4. washThe combined organic layers were washed with brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was triturated with methanol
  8. customto yield a pale brown solid
  9. customRecrystallisation from hot dichloromethane and methanol

Sources & evidence

ORD record
ord-8d37804937a247018ef8d47c8f1bcc48
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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