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

HRID 970731ノート

反応式

HRID 970731 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-35721a9e980a4ba78d298e2224b13448
出典データセット
uspto-grants-2007_12
特許番号
US07312236B2

反応ノート

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