HCID 89924005, compound → HCID 89938219, compound

HRID 2200361Notes

Reaction equation

HRID 2200361 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([CH3:20])([CH3:19])/[CH:15]=[CH:16]/[C:17]#[N:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>C(COC)OC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14]([CH3:20])([CH3:19])[CH2:15][CH2:16][C:17]#[N:18])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 89924005HCID 89924005, compound

Product 1

HCID 89938219HCID 89938219, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To the stirred solution of (E)-4-(4-(4-fluorophenyl)piperazin-1-yl)-4-methylpent-2-enenitrile (1.5 g), was added sodumborohydride (0.453 mg) in dimethoxyethane (30 ml) and stirred at room temperature for 1 hour before being heated to 75° C. for 2 h. The solution was cooled to room temperature and allowed to stirrer at 25° C. for 24 h then quenched with saturated ammonium chloride (50 mL). The aqueous phase was extracted with dichloromethane (3×50 ml). The organic phase was dried over sodium sulphate and concentrated under vacuum. The residue was purified by flash column chromatography using 20% ethyl acetate in hexane as an eluent to obtain the title compound (1.3 g, 58.6%).

Workup

  1. temperaturebefore being heated to 75° C. for 2 h
  2. temperatureThe solution was cooled to room temperature
  3. waitallowed to stirrer at 25° C. for 24 h
  4. customthen quenched with saturated ammonium chloride (50 mL)
  5. extractionThe aqueous phase was extracted with dichloromethane (3×50 ml)
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-1a4c9d5c7d194a6d8c3554b26c8ffea7
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

Loading…