Toluene → HCID 18940674, compound

HRID 355751Notes

Reaction equation

HRID 355751 reaction equation
[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.C1(C)C=CC=CC=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][C:30]=1[N:36]1[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]1>ClCCl.C(N(CC)CC)C>[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[CH:15][CH:14]=2)=[CH:31][C:30]=1[N:36]1[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 883374-Cyclohexylbenzoic acidHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 18940674HCID 18940674, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-Cyclohexylbenzoic acid (300 mg, 1.5 mmol) was heated at reflux with thionyl chloride (2 ml) and toluene (40 ml) for 2 h, and then evaporated to dryness under reduced pressure. 4-Methoxy-3-(4-methyl-1-piperazinyl)phenylamine (325 mg, 1.5 mmol) in dry dichloromethane (40 ml) was added with triethylamine (2 ml) and the mixture 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 flash column chromatography (silica, chloroform/methanol 5%) to afford the title compound (561 mg, 92%) which was crystallised from methanol/diethyl ether as the oxalate salt m.p. 117°-119° C.

Workup

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

Sources & evidence

ORD record
ord-b49adb1682b84888bb73f304ad919862
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

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