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

HRID 219883

Reaction equation

HRID 219883 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+].[C:17]([O:21][C:22](=[O:26])[CH2:23][CH2:24]Br)([CH3:20])([CH3:19])[CH3:18]>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])[CH2:24][CH2:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:26])#[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 solution of 3-[(methylamino)methyl]benzonitrile (6.1 g, 0.0417 mol) and sodium bicarbonate (7 g, 0.0834 mol) in acetonitrile (70 mL) under N2, was added tert-butyl-3-bromo-propanoate (7 mL, 0.0417 mol) in dropwise. After being stirred at RT for 12 h, the reaction mixture was filtered and the filterate was concentrated under reduced pressure. The obtained crude was purified using column chromatography on neutral silica gel (pet ether/EtOAc) to afford the title compound as a pale yellow liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.69-7.70 (s, 2H), 7.59-7.61 (m, 1H), 7.49-7.53 (m, 1H), 3.49 (s, 2H), 2.56-2.59 (m, 2H), 2.34-2.38 (m, 2H), 2.09 (s, 3H), 1.38 (s, 9H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filterate was concentrated under reduced pressure
  3. customThe obtained crude
  4. customwas purified

Sources & evidence

ORD record
ord-557cfc614035461eb285200d40656b02
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Linked notes

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