Sodium Hydroxide → HCID 89938248, compound

HRID 2200358Notes

Reaction equation

HRID 2200358 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([CH3:27])([CH3:26])[C:21](OCC)=[O:22])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[OH-].[Na+]>C(OCC)(=O)C>[F:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:15][CH2:16][N:17]([C:20]([CH3:27])([CH3:26])[CH2:21][OH:22])[CH2:18][CH2:19]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 89924015HCID 89924015, compound

Product 1

HCID 89938248HCID 89938248, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of lithium aluminium hydride (0.774 g, 20.4 mmol) in tetrahudrofuran (20 mL) was added ethyl 2-(4-(4-fluorophenyl)piperazin-1-yl)-2-methylpropanoate (prepared according to procedure reported in Bioorganic & Medical Chemistry, 2006, 14, 2725; 2.0 g, 6.79 mmol) in tetrahudrofuran (10 mL) was added slowly at 25° C. The resulting mixture was then stirred for 16 h. After completion of reaction, ethyl acetate (5 ml) was added followed by 1N Sodium hydroxide (20 ml) and allowed to stirred for 1 h. It was then passed through a celite bed and washed with ethyl acetate (100 ml. To the filtrate water (50 ml) was added and extracted with ethyl acetate (3×50 mL), combined organic layers was dried over sodium sulphate and concentrated to afford crude product. Crude product was purified by using silica gel (100-200 mesh) column chromatography using 5% methanol in dichloromethane as eluent to obtain the titled compound (1.5 g, 87.0%).

Workup

  1. additionwas added slowly at 25° C
  2. additionwas added
  3. stirringto stirred for 1 h
  4. washwashed with ethyl acetate (100 ml
  5. additionTo the filtrate water (50 ml) was added
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. dry with materialwas dried over sodium sulphate
  8. concentrationconcentrated
  9. customto afford crude product
  10. customCrude product was purified

Sources & evidence

ORD record
ord-6d759e8b9e3446dabb6126c17b6c90c8
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

Loading…