Triethylamine → HCID 21701695, compound

HRID 1596227Notes

Reaction equation

HRID 1596227 reaction equation
[CH2:1]([NH:8][C:9]([CH:11]1[CH2:16][N:15]([NH2:17])[CH2:14][CH2:13][N:12]1[C:18](=[O:20])[CH3:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>ClCCl>[C:18]([N:12]1[CH2:13][CH2:14][N:15]([NH:17][C:33](=[O:34])[C:32]2[CH:36]=[CH:37][C:29]([F:28])=[CH:30][CH:31]=2)[CH2:16][CH:11]1[C:9](=[O:10])[NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 21701679HCID 21701679, compound

Product 1

HCID 21701695HCID 21701695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of rac-N-benzyl-1-acetyl-4-aminopiperazine-2-carboxamide (274 mg) and triethylamine (0.28 ml) in dichloromethane (5 ml) was added 4-fluorobenzoyl chloride (0.13 ml) at 0° C. The mixture was stirred at ambient temperature for 1 hour, washed with water and brine. The organic layer was dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography eluting with a mixture of methanol and chloroform (1:9) to give crystals. Recrystallization of methanol, ethyl acetate and n-hexane gave rac-N-[4-acetyl-3-(N-benzylcarbamoyl)-1-piperazinyl]-4-fluorobenzamide (104 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography
  5. washeluting with a mixture of methanol and chloroform (1:9)
  6. customto give crystals
  7. customRecrystallization of methanol, ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-5ee48fb89d2042a29f846d09410f4684
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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