Hydrochloric Acid → 3-(4-Dimethylamino-cyclohex-1-enyl)-2-fluoro-phenylamine

HRID 970731노트

반응식

HRID 970731 반응식
Cl.C(=[N:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH2:27][CH2:26][CH:25]([N:28]([CH3:30])[CH3:29])[CH2:24][CH:23]=2)[C:17]=1[F:31])(C1C=CC=CC=1)C1C=CC=CC=1.[NH4+].[OH-]>C1COCC1>[CH3:29][N:28]([CH3:30])[CH:25]1[CH2:26][CH2:27][C:22]([C:18]2[C:17]([F:31])=[C:16]([NH2:15])[CH:21]=[CH:20][CH:19]=2)=[CH:23][CH2:24]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86611762Benzhydrylidene-(3-(4-dimethylamino-cyclohex-1-enyl)-2-fluoro-phenyl)-amine

생성물 1

HCID 588523563-(4-Dimethylamino-cyclohex-1-enyl)-2-fluoro-phenylamine수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add concentrated hydrochloric acid (2 mL) into a solution of the above benzhydrylidene-(3-(4-dimethylamino-cyclohex-1-enyl)-2-fluoro-phenyl)-amine (2.27 g, 5.7 mmol) in THF (20 mL) and heat at reflux for 1 hr. Basify the reaction mixture with conc. NH4OH and partition between saturated aqueous NaCl and DCM, dry the organic phase with anhydrous sodium sulfate, evaporate the solvent, and purify the residue by chromatography on a silica gel column (DCM: 2M NH3 in MeOH, gradient) to give the title compound (1.189 g): MS (ES): m/z=235 (M+H)+. 1H NMR (CDCl3): δ 6.85 (m, 1H), 6.64 (m, 1H), 6.87 (m, 1H), 5.87 (m, 1H), 3.70 (br s, 2H), 2.3-2.6 (m, 4H), 2.35 (s, 6H), 2.18 (m, 1H), 2.06 (m, 1H), 1.55 (m, 1H).

후처리

  1. temperatureheat
  2. temperatureat reflux for 1 hr
  3. custompartition between saturated aqueous NaCl and DCM
  4. dry with materialdry the organic phase with anhydrous sodium sulfate
  5. customevaporate the solvent
  6. custompurify the residue by chromatography on a silica gel column (DCM: 2M NH3 in MeOH, gradient)

출처 및 근거

ORD 기록
ord-35721a9e980a4ba78d298e2224b13448
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312236B2

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