Tetrahydrofuran → HCID 22264996, compound

HRID 915818Notes

Reaction equation

HRID 915818 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[Cl:12][C:13]1[CH:36]=[CH:35][C:16]([O:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)=O)=[CH:15][CH:14]=1.[OH-].[Na+]>O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][CH2:19][N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 3632922HCID 3632922, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22264996HCID 22264996, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of lithium aluminum hydride (0.29 g, 7 mmol)yin a solution of anhydrous THF (16 mL) was added 1-((4-chlorophenoxy)methyl)carbonyl-4-(4-fluorobenzyl)piperazine (0.36 g, 1.0 mmol, in 3 mL of THF). The resultant mixture was stirred at ambient temperature for 9 hours. At that time 0.3 mL of water and 0.3 mL of 15% aqueous NaOH solution were added and the resulting mixture stirred at ambient temperature. After 18 hours, the mixture was filtered through a short column of Celite (THF) and the filtrate concentrated in vacuo to afford 0.12 g of 1-(2-(4-chlorophenoxy)ethyl)-4-(4-fluorobenzyl)piperazine as a clear oil; NMR (CDCl3) 7.2 (m, 4), 7.0 (m, 2), 6.8 (m, 2), 4.0 (m, 2), 3.4 (m, 2), 2.8-2.4 (m, 10) ppm.

Workup

  1. filtrationthe mixture was filtered through a short column of Celite (THF)
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-e1832704dc864c1f831998dd0a57db20
Source dataset
uspto-grants-2007_09
Patent number
US07268140B2

Reaction notes

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