Sodium Iodide → Dpi-221

HRID 445022Notes

Reaction equation

HRID 445022 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C@H:9]([C:16]1[CH:28]=[CH:27][C:19]([C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[I-].[Na+].C(N(CC)CC)C.[F:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH2:42]Br.FC(Br)C1C=CC=CC=1>C(#N)C>[CH3:1][C@H:2]1[CH2:7][N:6]([CH2:42][C:41]2[CH:44]=[CH:45][CH:46]=[C:39]([F:38])[CH:40]=2)[C@H:5]([CH3:8])[CH2:4][N:3]1[C@H:9]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])=[CH:27][CH:28]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 680073-Fluorobenzyl bromideHCID 316418[Bromo(fluoro)methyl]benzeneHCID 102158644-((alpha-s)-alpha-((2s,5r)-2,5-Dimethyl-1-piperazinyl)benzyl)-n,n-diethylbenzamide

Product 1

HCID 9891642Dpi-221

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-((alpha-S)-alpha-((2S,5R)-2,5-dimethyl-1-piperazinyl)benzyl)-N,N-diethylbenzamide (9.128 g, 24.05 mmol) in acetonitrile (150 mL) was added to sodium iodide (360 mg, 2.4 mmol) and stirred under nitrogen during the addition of triethylamine (12 mL, 8.76 g, 86.6 mmol), followed by 3-fluorobenzyl bromide (5.9 mL, 9.09 g, 48.1 mmol). An immediate turbidity was observed on addition of the fluorobenzyl bromide, thickening to a white crystalline precipitate over one hour. The reaction mixture was stirred under nitrogen overnight at room temperature. The solvent was removed by evaporation, and saturated sodium bicarbonate solution (25 mL) was added to the residue. The copious white precipitate was collected by filtration, washed well with water and dried under vacuum at room temperature. (10.54 g, 89.2%). Calc. for C31H38FN3O 0.2 H2O: C, 75.79; H, 7.88; N, 8.55; F, 3.87. Found C, 75.80; H, 7.78; N, 8.49; F, 3.75%.

Workup

  1. customThe solvent was removed by evaporation, and saturated sodium bicarbonate solution (25 mL)
  2. additionwas added to the residue
  3. filtrationThe copious white precipitate was collected by filtration
  4. washwashed well with water
  5. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-d57cb1431af5487a8ec7ab2830986001
Source dataset
uspto-grants-2013_07
Patent number
US08476280B2

Reaction notes

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