Piperidine → N-(4-methoxyphenyl)piperidine

HRID 1596841Notes

Reaction equation

HRID 1596841 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]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]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 121674-ChloroanisoleHCID 23676156Sodium t-butoxide

Product 1

HCID 10130315N-(4-methoxyphenyl)piperidineYield 67%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

The general procedure from Example 1 was followed using 4-chloroanisole (171 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 4.0 mL of toluene. After 12 h, the reaction mixture was chromatographed with 5% ethyl acetate/hexane to give 128 mg (67% yield) of N-(4-methoxyphenyl)piperidine. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ 6.81 (d, J=9.11 Hz, 2H), 6.72 (d, J=9.11 Hz, 2H), 3.65 (s, 3H), 2.92 (t, J=5.46 Hz, 4H), 1.60 (m, 4H), 1.46 (m, 2H) ppm. 13C NMR (125 MHz, CDCl3): δ 153.5, 146.8, 118.6, 114.3, 55.4, 52.2, 26.1, 24.1 ppm.

Workup

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

Sources & evidence

ORD record
ord-f67890dfcd4c4213a114ff276bd10ee8
Source dataset
uspto-grants-2001_09
Patent number
US06291722B1

Reaction notes

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