Hydrochloric Acid → 1-((2,4-Difluorophenyl)methyl)piperazine dihydrochloride

HRID 2239786노트

반응식

HRID 2239786 반응식
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1.FC(F)(F)C(O)=O.[OH-].[Na+].[ClH:32]>C(Cl)Cl.C(Cl)Cl.CCOCC.CCOCC>[ClH:32].[ClH:32].[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 684130721-BOC-4-(2,4-difluorobenzyl)piperazine

생성물 1

HCID 669609111-((2,4-Difluorophenyl)methyl)piperazine dihydrochloride

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 21881112Ethyl ether methylene chloride용매

실험 절차

To a solution of 6.2 g (19.85 mmol) of the title A compound, t-butyl 4-(2,4-difluorobenzyl)piperazine-1-carboxylate in 50 mL of DCM at 0° C. is added 15 mL of trifluoroacetic acid. The reaction mixture is warmed to RT and stirred for 1 h, and 10 mL of 1 N aqueous sodium hydroxide (NaOH) are added. The mixture is extracted with 2×100 mL of DCM and the organic layer is washed with water, dried over anhydrous MgSO4 and evaporated to dryness in vacuo. The residue is dissolved in a mixture of DCM-Et2O and two equivalents of HCl in Et2O are added, the precipitate solid is collected by filtration and washed with acetone to afford 4-(2,4-difluorobenzyl)piperazine dihydrochloride as a white solid: m.p=237° C. LC/MS (M+1=213.1). 1H NMR (DMSO-d6, 400 MHz) δ 3.44 (m, 8H), 4.39 (s, 2H), 7.25 (dt, 1H, J=8.4 Hz and 1.6 Hz), 7.43 (dt, 1H, J=9.2 Hz and 2.0 Hz), 7.84 (dd, 1H, J=15.2 Hz and 8.4 Hz), 9.84 (br s, NH). Anal. calculated for (C11H14F2N2, 2HCl+0.25 H2O) C, 45.61; H, 5.74; Cl, 24.48; F, 13.12; N, 9.67; O, 1.38. Found C, 45.56; H, 5.90; N, 9.68.

후처리

  1. extractionThe mixture is extracted with 2×100 mL of DCM
  2. washthe organic layer is washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated to dryness in vacuo
  5. additionare added
  6. filtrationthe precipitate solid is collected by filtration
  7. washwashed with acetone

출처 및 근거

ORD 기록
ord-0a1026c7c1394bd8a6fa67cae82ee66b
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723343B2

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