4-Chlorotoluene → HCID 10130194, compound

HRID 1884176Notes

Reaction equation

HRID 1884176 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](Cl)=[CH:4][CH:3]=1.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78104-ChlorotolueneHCID 8082PiperidineHCID 23676156Sodium t-butoxide

Product 1

HCID 10130194HCID 10130194, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

The general procedure from Example 1A was followed using 4-methyl-chlorobenzene (152 mg, 1.2 mmol) and piperidine (100 μl, 1.0 mmol) with Pd2(dba)3 (20 mg, 0.0218 mmol) and (Me3C)2PH(O) (14.5 mg, 0.0878 mmol) and NaOtBu (144 mg, 1.5 mmol) in 3.0 mL of toluene. After 12 h, the reaction mixture was chromatographed with 5% ethyl acetate/hexane to give 106 mg (δ1% yield) of N-(4-methylphenyl)piperidine. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ6.92 (d, J=8.4 Hz, 2H), 6.72 (d, J=8.5 Hz, 2H), 2.95 (t, J=5.5 Hz, 4H), 2.13 (s, 3H), 1.58 (m, 4H),1.43 (m, 2H) ppm. 13C NMR (125 MHz, CDCl3): δ150.3, 129.5, 128.6, 116.9, 51.2, 25.9, 24.3, 20.3 ppm. MS: Calculated for C12H17N(M+): 175.1. Found: 176.1 (M++H).

Workup

  1. customthe reaction mixture was chromatographed with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ccdfa3ebca2c41a9ad28c379450470de
Source dataset
uspto-grants-2004_07
Patent number
US06762330B2

Reaction notes

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