tert-Butyl 3-bromopropionate → tert-Butyl 3-[(3-cyanobenzyl)(methyl)amino]propanoate

HRID 2410504Notes

Reaction equation

HRID 2410504 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8].C(=O)(O)[O-].[Na+].Br[CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>C(#N)C>[C:7]([C:6]1[CH:5]=[C:4]([CH:11]=[CH:10][CH:9]=1)[CH2:3][N:2]([CH3:1])[CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])#[N:8]

Participants

5

Reactant 3

HCID 256128tert-Butyl 3-bromopropionateHCID 4575953-(Methylaminomethyl)benzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 66678103tert-Butyl 3-[(3-cyanobenzyl)(methyl)amino]propanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 3-[(methylamino)methyl]benzonitrile (6.1 g, 41.7 mmol) and sodium bicarbonate (7.0 g, 83.4 mmol) in ACN (70 mL) was added dropwise tert-butyl 3-bromo-propanoate (7 mL, 41.7 mol). After being stirred at RT for 12 hours, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica, pet ether/EtOAc) to afford the title compound as a pale yellow liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.70 (s, 2H), 7.60 (m, 1H), 7.51 (m, 1H), 3.49 (s, 2H), 2.58 (m, 2H), 2.36 (m, 2H), 2.09 (s, 3H), 1.38 (s, 9H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by chromatography (silica, pet ether/EtOAc)

Sources & evidence

ORD record
ord-7c06ab2e3027439e843d07358671091d
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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