3-(1,3-Dioxan-2-yl)aniline → HCID 178512007, compound

HRID 659125Notes

Reaction equation

HRID 659125 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=1)[NH2:10].C[Al](C)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][C:20]=1[C:31]#[N:32]>C1(C)C=CC=CC=1.CCCCCCC.C(Cl)Cl.CO>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([NH:10][C:31]([C:20]2[CH:21]=[C:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:23]=[CH:24][C:19]=2[F:18])=[NH:32])[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 6016073-(1,3-Dioxan-2-yl)anilineHCID 16682925TrimethylaluminumHCID 46314739HCID 46314739, compound

Product 1

HCID 178512007HCID 178512007, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 8900HeptaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To 3-(1,3-dioxan-2-yl)aniline (55) (336 mg, 1.87 mmol) in toluene (7.5 mL) cooled to 0° C. was added a 2M trimethylaluminum solution in heptane (1.32 mL) dropwise and the resulting mixture was stirred at ambient temperature for 3.5 hours. The nitrile (54) (370 mg, 1.88 mmol) in toluene (7.5 mL) was added and the reaction heated to 70° C. overnight. The reaction was then cooled, poured onto a slurry of silica in DCM/MeOH and the organics flushed through with further DCM/MeOH. The filtrate was concentrated in vacuo and the residue purified by column chromatography using a gradient of EtOAc in heptane (5-100%) to yield the title compound. Yield: 378 mg, 53%; LC-MS tr 1.32 min; HPLC Purity: 71%; MS (ES+) m/z 377 (M+H)

Workup

  1. temperaturethe reaction heated to 70° C. overnight
  2. temperatureThe reaction was then cooled
  3. customthe organics flushed through with further DCM/MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-6f27497884c9483ebcf2bfaaa9559680
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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