1-(3-Bromo-2-fluoro-phenyl)-4-dimethylamino-cyclohexanol → (4-(3-Bromo-2-fluoro-phenyl)-cyclohex-3-enyl)-dimethyl-amine

HRID 970729Notes

Reaction equation

HRID 970729 reaction equation
[Br:1][C:2]1[C:3]([F:18])=[C:4]([C:8]2(O)[CH2:13][CH2:12][CH:11]([N:14]([CH3:16])[CH3:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([F:18])=[C:4]([C:8]2[CH2:13][CH2:12][CH:11]([N:14]([CH3:15])[CH3:16])[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 588523751-(3-Bromo-2-fluoro-phenyl)-4-dimethylamino-cyclohexanol

Product 1

HCID 58852349(4-(3-Bromo-2-fluoro-phenyl)-cyclohex-3-enyl)-dimethyl-amineYield 88.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Heat 1-(3-bromo-2-fluoro-phenyl)-4-dimethylamino-cyclohexanol (preparation 6, 2.04 g, 6.45 mmol) and p-TsOH monohydrate (3.07 g, 16 mmol) in toluene (50 mL) at reflux for 2 hr. Partition the reaction mixture between saturated aqueous NaCl and ethyl acetate, 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 product (1.70 g): MS (ES): m/z=300 (M+H)+ and 298 (M−H)−. 1HNMR (CDCl3): δ 7.39 (m, 1H), 7.14 (m, 1H), 6.94 (m, 1H), 5.88 (m, 1H), 2.60-2.38 (m, 4H), 2.35 (s, 6H), 2.20 (m, 1H), 2.08 (m, 1H), 1.56 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-07b3143bdb84403cae31ad1260769411
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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