Benzylamine → Tert-butyl 2-(benzylamino)acetate

HRID 329006Notes

Reaction equation

HRID 329006 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C1C=CC=CC=1.[OH-].[Na+]>[C:14]([O:13][C:11](=[O:12])[CH2:10][NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 66052tert-Butyl chloroacetate

Product 1

HCID 11020442Tert-butyl 2-(benzylamino)acetateYield 89%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To 71.0 g of benzylamine in 100 ml of benzene was added with stirring 25.0 g of tert-butyl chloroacetate over a period of 30 minutes, while maintaining the temperature at 30°-70° C. The reaction mixture was held at 70° C for an additional 1 hour. At the end of this period, the reaction mixture was taken up in 70 ml of 2N NaOH solution and 80 ml of benzene, transferred into a separatory funnel and well shaken. The benzene solution was separated, washed with water, dried over anhydrous sodium sulfate and filtered. After evaporation of benzene, the residue was distilled under reduced pressure to give 32.7 g (89.0 percent) of N-benzylglycine tert-butyl ester, B.P. 120°-125° C/ 2 mmHg.

Workup

  1. temperaturewhile maintaining the temperature at 30°-70° C
  2. customThe benzene solution was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customAfter evaporation of benzene
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-128b55f597bd47f3a3002985b2d0075c
Source dataset
uspto-grants-1977_04
Patent number
US04018915

Reaction notes

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