Phenethylamine → Tert-butyl 2-[(2-phenylethyl)amino]acetate

HRID 1264390Notes

Reaction equation

HRID 1264390 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>C1(C)C=CC=CC=1>[C:15]([O:14][C:12](=[O:13])[CH2:11][NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 14461641Tert-butyl 2-[(2-phenylethyl)amino]acetateYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 12.6 ml (100 mmol) phenethylamine in 50 ml toluene was treated at RT with 7.4 ml (200 mmol) tert-butyl bromoacetate and heated at 95° C. for 4 h. After cooling (0° C.), filtration and evaporation of the filtrate, the residue was suspended in pentane, cooled (0° C.), filtrated and evaporated to give 11.5 g (98%) of phenethylamino-acetic acid tert-butyl ester as an oil, MS: 236 (MH+).

Workup

  1. temperatureAfter cooling
  2. filtration(0° C.), filtration and evaporation of the filtrate
  3. temperaturecooled (0° C.)
  4. filtrationfiltrated
  5. customevaporated

Sources & evidence

ORD record
ord-6d65350112044a5fbc1818be7066ed20
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

Loading…