Triethylamine → N-benzoyl alpha(N,N-dimethylaminomethyl) phenethylamine

HRID 1388628Notes

Reaction equation

HRID 1388628 reaction equation
[C:1]([NH:9][C@H:10]([C:18](O)=O)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([N:23](CC)[CH2:24]C)C>>[C:1]([NH:9][CH:10]([CH2:18][N:23]([CH3:24])[CH3:21])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8471TriethylamineHCID 97370Benzoyl-L-phenylalanine

Product 1

HCID 13069511N-benzoyl alpha(N,N-dimethylaminomethyl) phenethylamineYield 81%

Conditions

Temperature
0 °C

Procedure

To a solution of 26.5 g of N-benzoyl phenylalanine (XIII) in 200 ml of T.H.F. are added 11 g of triethylamine, it is cooled to 0° C. and 11 g of ethyl chloroformiate are added. After 30 mn at 0° C., a solution of 4.5 g of diethyllamine in 50 ml of T.H.F. is added, then it is left for 2 hours at ambient temperature. Then the solvent is evaporated, the residue taken up in water, extracted with chloroform, dried on sodium sulfate, filtered and the filtrate evaporated. Thus, the expected product was obtained with a yield of 81%.

Workup

  1. addition11 g of ethyl chloroformiate are added
  2. customat 0° C.
  3. additionis added
  4. customThen the solvent is evaporated
  5. extractionextracted with chloroform
  6. customdried on sodium sulfate
  7. filtrationfiltered
  8. customthe filtrate evaporated

Sources & evidence

ORD record
ord-32c590790dc540aa8f70bd65b63849f6
Source dataset
uspto-grants-1984_02
Patent number
US04431851

Reaction notes

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