Sodium Iodide → Dpi-221

HRID 1795904Notes

Reaction equation

HRID 1795904 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-221Yield 89.9%

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) added to the residue. The copious white precipitate was filtered off, washed well with water and dried under vacuum at room temperature to give 4-((alpha-S)-alpha-((2S,5R)-2,5-dimethyl-4-(3-fluorobenzyl)-1-piperazinyl)benzyl)-N,N-diethylbenzamide (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. additionadded to the residue
  3. filtrationThe copious white precipitate was filtered off
  4. washwashed well with water
  5. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-505697f947f944f58fe8de327b56b199
Source dataset
uspto-grants-2006_04
Patent number
US07030124B2

Reaction notes

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