4-(Bromomethyl)benzonitrile → HCID 9906185, compound

HRID 1016289Notes

Reaction equation

HRID 1016289 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([CH2:12][CH2:11][C:10](=[O:13])[C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=3[NH:7]2)[CH2:3][CH2:2]1.[C:18]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1)#[N:19]>C1COCC1>[C:18]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:1]2[CH2:6][CH2:5][C:4]3([CH2:12][CH2:11][C:10](=[O:13])[C:9]4[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=4[NH:7]3)[CH2:3][CH2:2]2)=[CH:22][CH:21]=1)#[N:19]

Participants

4

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 10130807HCID 10130807, compound

Product 1

HCID 9906185HCID 9906185, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of diamine 11 (5 mg, 0.022 mmol) in anhydrous THF and 4-cyanobenzyl bromide (5 mg, 0.026 mmol) was agitated at room temperature for 16 h, and piperidinomethyl polystyrene N-2-(mercaptoethyl) aminoethyl polystyrene (26 mg, 0.033 mmol) was then added. The reaction was agitated for another 12 h and then filtered. The filtrate was concentrated to yield 24 (5 mg, 0.014 mmol, 66%) as an oil. LRMS: M+345.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d3dc70d88d00421b82857d29fd2a400c
Source dataset
uspto-grants-2002_11
Patent number
US06476019B1

Reaction notes

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