Piperidine → 1-(Naphthalen-2-yl)piperidine

HRID 399303

Reaction equation

HRID 399303 reaction equation
CC(C)([O-])C.[Na+].[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1OS(C(F)(F)F)(=O)=O.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>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.[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

8

Reactant 4

HCID 8082PiperidineHCID 45463412-Naphthyl TrifluoromethanesulfonateHCID 23676156Sodium t-butoxideHCID 178506046HCID 178506046, compound

Product 1

HCID 2307091-(Naphthalen-2-yl)piperidineYield 77%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
105 °C

Procedure

The method described in this example is representative of method "A". Into a screw-capped test tube were weighed 8.6 mg (0.015 mmol) Pd(dba)2, 12.8 mg (0.023 mmol) DPPF, and 44.3 mg (0.462 mmol) sodium t-butoxide (NaO-t-Bu). The solid materials were suspended in 8 ml of toluene. 2-Naphthyltriflate (85.0 mg, 0.308 mmol) was dissolved in 1 ml of toluene and added to the test tube. The test tube was sealed with a cap containing a polytetrafluoroethylene (PTFE) septum and removed from the dry box. Piperidine (40.0 μl, 0.462 mmol) was added to the test tube by syringe. The reaction mixture was heated at 105° C. for 5 hours. Thin layer chromatography (TLC) of the reaction mixture indicated complete consumption of the naphthyltriflate. The reaction mixture was cooled to room temperature, and the volatile materials were removed by rotary evaporation. Sublimation (120° C., 0.1 torr) of the resulting residue afforded N-(2-naphthyl)piperidine as a white solid (50.0 mg, 77% yield).

Workup

  1. customInto a screw-capped test tube were weighed
  2. additionadded to the test tube
  3. customThe test tube was sealed with a cap
  4. customremoved from the dry box
  5. customconsumption of the naphthyltriflate
  6. temperatureThe reaction mixture was cooled to room temperature
  7. customthe volatile materials were removed by rotary evaporation

Sources & evidence

ORD record
ord-e8569e87b83f41cf84c4832f320de4b8
Source dataset
uspto-grants-1998_10
Patent number
US05817877

Linked notes

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