Toluene → HCID 10130194, compound

HRID 399304Notes

Reaction equation

HRID 399304 reaction equation
O(C(C)(C)C)[Na].[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[C:13]1([CH3:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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]>[CH3:19][C:13]1[CH:18]=[CH:17][C:16]([N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 1140Toluene2×HCID 8082PiperidineHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 10130194HCID 10130194, compoundYield 77%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

This example is representative of procedure "B". Into a screw-capped test tube were weighed 29 mg (0.052 mmol) Pd(dba)2, 55 mg (0.10 mmol) DPPF, and 144 mg (1.5 mmol) NaO-t-Bu. The solid materials were suspended in 12 ml of toluene. 4-Methylphenyltriflate (240 mg, 1.0 mmol) was dissolved in 1 ml of toluene and added to the test tube. The test tube was sealed with a cap containing a PTFE septum and removed from the dry box. Piperidine (148 μl, 1.5 mmol) was added to the test tube by syringe. The reaction mixture was heated at 100° C. for 5 hours. TLC of the reaction mixture indicated complete consumption of the starting triflate. The reaction mixture was cooled to room temperature, and the mixture was absorbed onto silica gel. Chromatography on a silica gel column using 50:1 hexanes:diethyl ether afforded 1-(4-methylphenyl)piperidine as a clear oil. (135 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 starting triflate
  6. temperatureThe reaction mixture was cooled to room temperature
  7. customthe mixture was absorbed onto silica gel

Sources & evidence

ORD record
ord-b89bc8900fd14d55812d834afc2c470e
Source dataset
uspto-grants-1998_10
Patent number
US05817877

Reaction notes

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