HCID 86059385, compound → HCID 58852350, compound

HRID 970733Notes

Reaction equation

HRID 970733 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2(O)[CH2:13][CH2:12][CH:11]([N:14]([CH3:16])[CH3:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[CH2:13][CH2:12][CH:11]([N:14]([CH3:16])[CH3:15])[CH2:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86059385HCID 86059385, compound

Product 1

HCID 58852350HCID 58852350, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Mix the above 1-(6-bromo-pyridin-2-yl)-4-dimethylamino-cyclohexanol (7 g, 23.4 mmol), p-toluenesulfonic acic monohydrate (15.3 g, 80.5 mmol), anhydrous toluene (600 mL). Heat at reflux for 16 hr. with a Dean Stark trap. Cool down to room temperature. Concentrate under reduced pressure. Partition between ethyl acetate and a 2M NaOH solution. Separate the organic layer, extract the aqueous layer twice with ethyl acetate. Combine the organic fractions, dry over sodium sulfate and concentrate to a residue. Purify the residue by chromatography (silica gel, 6% 2M NH3-MeOH in DCM) to yield (4-(6-bromo-pyridin-2-yl)-cyclohex-3-enyl)-dimethyl-amine (5.3 g, 81% yield): MS (ES): m/z=299 (M+H)+; 1H NMR (CDCl3): δ 7.45 (m, 1H), 7.27 (m, 2H), 6.72 (m, 1H), 2.69 (m, 1H), 2.45 (m, 3H), 2.33 (s, 6H), 2.21 (m, 2H), 1.58 (m, 1H).

Workup

  1. temperatureHeat
  2. temperatureat reflux for 16 hr
  3. concentrationConcentrate under reduced pressure
  4. customPartition between ethyl acetate
  5. customSeparate the organic layer
  6. extractionextract the aqueous layer twice with ethyl acetate
  7. dry with materialdry over sodium sulfate
  8. concentrationconcentrate to a residue
  9. customPurify the residue by chromatography (silica gel, 6% 2M NH3-MeOH in DCM)

Sources & evidence

ORD record
ord-4fd18b4e669e45da8f12de3d563897e9
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

Loading…