Potassium Carbonate → HCID 11121342, 화합물

HRID 1457808노트

반응식

HRID 1457808 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 11121342HCID 11121342, 화합물수율 18%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-8d37804937a247018ef8d47c8f1bcc48
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849765

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