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

HRID 970731Notes

Reaction equation

HRID 970731 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-35721a9e980a4ba78d298e2224b13448
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

Loading…