Sodium Hydroxide → HCID 12637767, compound

HRID 1616646Notes

Reaction equation

HRID 1616646 reaction equation
[CH3:1][N:2]1[CH:7]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[C:5]([CH3:16])[CH2:4][CH2:3]1.CN1CC=C(C)CC1CCC1C=CC=CC=1.[OH-].[Na+]>O>[CH3:16][C:5]12[CH2:6][CH:7]([N:2]([CH3:1])[CH2:3][CH2:4]1)[CH2:8][CH2:9][C:10]1[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12637766HCID 12637766, compoundHCID 58123984HCID 58123984, compound

Product 1

HCID 12637767HCID 12637767, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
150 °C

Procedure

A mixture of 1,4-dimethyl-6-phenethyl-1,2,3,6-tetrahydro-pyridine and 1,4-dimethyl-2-phenethyl-1,2,3,6-tetrahydro-pyridine (ca. 3:1, 1.0 g) dissolved in polyphosphoric acid (5 mL) is stirred at 150° C. for 2 d. After cooling to ca. 80° C., water (30 mL) is added and the mixture is stirred vigorously for another 5 min. Then, the mixture is cooled in an ice bath, more water is added, and the mixture is basified using 40% NaOH in water. The resulting mixture is extracted with ethyl acetate, the combined organic extracts are washed with brine and dried (MgSO4). The solvent is removed under reduced pressure to yield the title compound.

Workup

  1. temperatureAfter cooling to ca. 80° C.
  2. stirringthe mixture is stirred vigorously for another 5 min
  3. temperatureThen, the mixture is cooled in an ice bath
  4. extractionThe resulting mixture is extracted with ethyl acetate
  5. washthe combined organic extracts are washed with brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-e93e7ac4047c474a9fcea9c5cbc17aaa
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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