Triethylamine → 4-Benzyl-1-[2-(2-fluorophenyl)propanoyl]piperazine

HRID 1600837Notes

Reaction equation

HRID 1600837 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([OH:11])=O.[CH2:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH2:13]([N:20]1[CH2:25][CH2:24][N:23]([C:9](=[O:11])[CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH3:12])[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184215882-(2-Fluoro-phenyl)-propionic acid

Product 1

HCID 218308564-Benzyl-1-[2-(2-fluorophenyl)propanoyl]piperazineYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Fluorophenyl)propanoic acid (7.7 g, 0.046 mol), 1-benzylpiperazine (8.0 g, 0.045 mol), triethylamine (4.6 g, 0.046 mol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (9.6 g, 0.050 mol) were dissolved in dichloromethane (150 ml) and stirred at room temperature for 18 h. The solution was evaporated and the residue diluted with water and extracted with brine, dried and evaporated. Chromatography on silica gel with dichloromethane-methanol (97:3) yielded 4-benzyl-1-[2-(2-fluorophenyl)propanoyl]piperazine (5.54 g, 38%) as an oil.

Workup

  1. customThe solution was evaporated
  2. additionthe residue diluted with water
  3. extractionextracted with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-170de012ad3c4b81969daf35188024b9
Source dataset
uspto-grants-1999_11
Patent number
US05977116

Reaction notes

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