Phenethylamine → N-Phenethylglycine benzyl ester hydrochloride

HRID 1940493Notes

Reaction equation

HRID 1940493 reaction equation
[CH2:1]([O:8][C:9](=[O:12])[CH2:10]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]([NH2:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl:22]Cl>C(Cl)Cl>[ClH:22].[CH2:1]([O:8][C:9](=[O:12])[CH2:10][NH:21][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 24526ChlorineHCID 62576Benzyl bromoacetate

Product 1

HCID 69862422N-Phenethylglycine benzyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of benzyl-2-bromoacetate (3.3 ml, 20.0 mmol) in CH2 Cl2 (30 ml) was added drop-wise to a solution of phenethylamine (12.6 ml, 100 mmol) in CH2Cl2 (30 ml) stirring at 0° C. After warming to room temperature the reaction was stirred for 24 hours, then filtered and the solvent evaporated in vacuo. The resulting residue was dissolved in ethyl acetate, and washed with brine and dried over sodium sulfate. The ethyl acetate was evaporated in vacuo. The crude material was purified using silica gel flash column chromatography eluting sequentially with hexane and ethyl acetate-hexane (9:1, v/v). The fraction containing the product had traces of benzyl-2-bromoacetate as an impurity. This portion was redissolved in CHCl3 and washed with 1N HCl. The chloroform layer was dried and the HCl salt was precipitated with petroleum ether. Yield 2.3 g colorless solid. 1H NMR (CDCl3) δ 1.95 (br s, 1H), 2.73-2.9 (m, 3H), 3.44 (s, 2H), 5.12 (s, 2H), 7.13-7.36 (m, 10H). 13C NMR (CDCl3) 6 36.17, 50.46, 50.63, 66.32, 26.06, 128.18, 128.3, 128.4, 128.50, 135.4, 139.4, 171.88.

Workup

  1. temperatureAfter warming to room temperature the reaction
  2. stirringwas stirred for 24 hours
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. dissolutionThe resulting residue was dissolved in ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. customThe ethyl acetate was evaporated in vacuo
  9. customThe crude material was purified
  10. washeluting sequentially with hexane and ethyl acetate-hexane (9:1
  11. additionThe fraction containing the product
  12. dissolutionThis portion was redissolved in CHCl3
  13. washwashed with 1N HCl
  14. dry with materialThe chloroform layer was dried
  15. customthe HCl salt was precipitated with petroleum ether

Sources & evidence

ORD record
ord-c680a89483d445e3b52cc7819d0e3f64
Source dataset
uspto-grants-1997_12
Patent number
US05700779

Reaction notes

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