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

HRID 2164465Notes

Reaction equation

HRID 2164465 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 phenyalanine (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 chlorofrom, dried on sodium sulfate, filtered and the filtrate evaporated. Thus, the expected product was obtained with a yield of 81% Melting point: 150° C.

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 chlorofrom
  6. customdried on sodium sulfate
  7. filtrationfiltered
  8. customthe filtrate evaporated

Sources & evidence

ORD record
ord-46d1dabeada1439ea59f3ba214a23cf4
Source dataset
uspto-grants-1985_03
Patent number
US04504663

Reaction notes

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