Water → 1-(1,4-Benzodioxan-5-yl)-4-cyanomethylpiperazine

HRID 381262Notes

Reaction equation

HRID 381262 reaction equation
Br[CH2:2][C:3]#[N:4].[O:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:9]=2[O:8][CH:7]=[CH:6]1.C(N(CC)CC)C.O>CN(C)C=O>[O:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([N:15]3[CH2:20][CH2:19][N:18]([CH2:2][C:3]#[N:4])[CH2:17][CH2:16]3)[C:9]=2[O:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11534BromoacetonitrileHCID 10398473Piperazine, 1-(1,4-benzodioxin-5-yl)-

Product 1

HCID 106112891-(1,4-Benzodioxan-5-yl)-4-cyanomethylpiperazineYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of bromoacetonitrile (2.38 g, 19.86 mmol), benzodioxin-5-ylpiperazine (5.1 g, 19.86 mmol) and triethylamine (11.05 mL, 79.4 mmol) in dimethylformamide (50 mL) was stirred under a nitrogen atmosphere at 70° C. for 3 days. Water (300 mL) was added and the product extracted into ethyl acetate (6×50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL) and dried over anhydrous sodium sulfate. Filtration and concentration on a rotary evaporator gave the desired compound as a light yellow oil which solidified on standing (5.1 g, 99% yield). The compound was isolated as its hydrochloride salt by treatment in ethyl acetate with ethereal HCl to yield a light yellow solid, mp=193-194° C.; MS (+) ESI m/z=260 (M+H)+.

Workup

  1. extractionthe product extracted into ethyl acetate (6×50 mL)
  2. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationFiltration and concentration
  5. customon a rotary evaporator

Sources & evidence

ORD record
ord-2a3fe0a0ac5745ca81942cca0c180ec9
Source dataset
uspto-grants-2001_10
Patent number
US06306859B1

Reaction notes

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