Water → Tert-butyl [(3-cyanobenzyl)(methyl)amino]acetate

HRID 219849Notes

Reaction equation

HRID 219849 reaction equation
Cl.[C:2]([O:6][C:7](=[O:11])[CH2:8][NH:9][CH3:10])([CH3:5])([CH3:4])[CH3:3].[CH2:12](N(CC)CC)C.BrC[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[C:24]#[N:25].O>C(#N)C>[C:24]([C:23]1[CH:22]=[C:21]([CH:28]=[CH:27][CH:26]=1)[CH2:10][N:9]([CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:11])[CH3:12])#[N:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 11252350Sarcosine t-butyl ester hydrochloride

Product 1

HCID 77231477Tert-butyl [(3-cyanobenzyl)(methyl)amino]acetateYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of sarcosine tert-butyl ester hydrochloride (8.1 g, 44.9 mmol) and triethylamine (17 mL, 122.4 mmol) in acetonitrile (100 mL) under N2, was added 3-(bromomethyl)benzonitrile (8 g, 40.8 mmol) portionwise over a period of 10 min at 0° C. After being stirred at RT for 3 h, the reaction mixture was poured into water and extracted with DCM. Then the organic layer was washed with brine and dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a pale green liquid (9 g, 85%). 1H NMR (DMSO-d6, 400 MHz) δ 7.71-7.72 (2H, m), 7.63-7.65 (1H, m), 7.53-7.55 (1H, m), 3.66 (2H, s), 3.18 (2H, s), 2.22 (3H, s), 1.41 (9H, s).

Workup

  1. extractionextracted with DCM
  2. washThen the organic layer was washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8aedd54098e04524ab895d97a129bbb5
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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