Benzylamine → HCID 10585850, compound

HRID 1834205Notes

Reaction equation

HRID 1834205 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:10]([CH3:18])[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])[C@H:10]([CH3:18])[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 523713HCID 523713, compound

Product 1

HCID 10585850HCID 10585850, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To 65.0 g of benzylamine in 100 ml of benzene was added with stirring 25.0 g of tert-butyl 2-chloropropionate 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 one 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 33.2 g (90.0 percent) of N-benzylalanine tert-butyl ester, B.P. 164° C/14 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-b22ff65d09054813bd2ee70628c99b20
Source dataset
uspto-grants-1978_01
Patent number
US04069317

Reaction notes

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