4-Fluorobenzoyl chloride → HCID 18940679, compound

HRID 355749Notes

Reaction equation

HRID 355749 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=1[N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1>ClCCl.C(N(CC)CC)C>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:15][C:14]=1[N:20]1[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]1

Participants

5

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 18940679HCID 18940679, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-Fluorobenzoyl chloride (0.23 ml, 1.95 mmol) with 4-methoxy-3-(4-methyl-1-piperazinyl)phenylamine (400 mg, 1.95 mmol) in dry dichloromethane (40 ml) and triethylamine (1 ml) was stirred for 1 h. The solution was partitioned between dichloromethane (40 ml) and saturated aqueous potassium carbonate (40 ml), the organic solution dried (sodium sulphate) and evaporated to dryness under reduced pressure to afford an oil, which was purified by column chromatography (silica, chloroform,/methanol 5%) to afford the tide compound (595 mg, 89%) which was crystallised from methanol/diethyl ether as the oxalate salt.

Workup

  1. customThe solution was partitioned between dichloromethane (40 ml) and saturated aqueous potassium carbonate (40 ml)
  2. dry with materialthe organic solution dried (sodium sulphate)
  3. customevaporated to dryness under reduced pressure
  4. customto afford an oil, which
  5. customwas purified by column chromatography (silica, chloroform,/methanol 5%)

Sources & evidence

ORD record
ord-b04348bc936847acb2362511233bf442
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

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