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

HRID 572581Notes

Reaction equation

HRID 572581 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 ACN (100 mL) was added 3-(bromomethyl)benzonitrile (8.0 g, 40.8 mmol) portionwise over a period of 10 minutes at 0° C. After being stirred at RT for 3 hours, the reaction mixture was poured into water and extracted with DCM. Then the organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a pale green liquid (9.0 g, 85%). 1H NMR (DMSO-d6, 400 MHz) δ 7.72 (2H, m), 7.64 (1H, m), 7.54 (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-5a2d354fac644ae9a30f05d029cc8f2b
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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