Dichloromethane → 1-((3-Methylbenzo[b]thiophen-2-yl)methyl)piperazine dihydrochloride

HRID 2239789노트

반응식

HRID 2239789 반응식
[CH3:1][C:2]1[C:3]2[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=2[S:5][C:6]=1[CH2:7][N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+].C(Cl)[Cl:38]>>[ClH:38].[ClH:38].[CH3:1][C:2]1[C:3]2[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=2[S:5][C:6]=1[CH2:7][N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1

참가 물질

5

반응물 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68415560t-Butyl 4-((3-methylbenzo[b]thiophen-2-yl)methyl)piperazine-1-carboxylate

생성물 1

HCID 684137241-((3-Methylbenzo[b]thiophen-2-yl)methyl)piperazine dihydrochloride

실험 절차

The title A compound, t-butyl 4-((3-methylbenzo[b]thiophen-2-yl)methyl)piperazine-1-carboxylate is dissolved in dry DCM (50 mL), and 5 equiv. of TFA are added at 0° C. The reaction mixture is stirred at RT for 3 h. After the solvent is evaporated in vacuo, the residue is trituated in Et2O, and the precipitate that forms is collected by filtration, washed with EtOH and dried in a vacuum oven at 40° C. overnight to give a hygroscopic solid. The solid is treated with sodium bicarbonate solution, and extracted with EtOAc. The organic layer is evaporated in vacuo, and the residue is dissolved in Et2O and treated with a solution of hydrochloric acid in Et2O. The precipitated solid is collected by filtration and dried to give 1-((3-methylbenzo [b]thiophen-2-yl)methyl)piperazine dihydrochloride: LC/MS (M+1=247.1). 1H NMR (DMSO-d6, 200 MHz) δ 2.48 (s, 3H), 3.39 (m, 4H), 3.54 (m, 4H), 4.63 (s, 2H), 7.45 (m, 2H), 7.84 (d, 1H, J=7.2 Hz), 7.95 (d, 1H, J=7.2 Hz), 9.52 (br s, NH). Anal. calculated for (C14H18N2S 2HCl): C, 52.66; H, 6.31; Cl, 22.21; N, 8.77; S, 10.04. Found: C, 52.70; H, 6.58; N, 8.77; S, 9.70.

후처리

  1. customAfter the solvent is evaporated in vacuo
  2. filtrationthe precipitate that forms is collected by filtration
  3. washwashed with EtOH
  4. customdried in a vacuum oven at 40° C. overnight
  5. customto give a hygroscopic solid
  6. extractionextracted with EtOAc
  7. customThe organic layer is evaporated in vacuo
  8. dissolutionthe residue is dissolved in Et2O
  9. additiontreated with a solution of hydrochloric acid in Et2O
  10. filtrationThe precipitated solid is collected by filtration
  11. customdried

출처 및 근거

ORD 기록
ord-56442da7b6d64b9487ef3bbbff457b4e
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723343B2

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