Benzhydrol → 4-Benzhydryloxypiperidine

HRID 1383452Notes

Reaction equation

HRID 1383452 reaction equation
[CH:1]([OH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:1]([O:14][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7037BenzhydrolHCID 79341Piperidin-4-olHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 30175844-BenzhydryloxypiperidineYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a round bottom flask, benzhydrol (1.84 g, 10 mmol, 1.0 eq.), 4-hydroxypiperidine (1.01 g, 10 mmol, 1.0 eq.), and p-toluenesulfonic acid monohydrate (2.09 g, 1.1 eq.) were suspended in toluene (400 ml). The mixture was refluxed with a Dean-Stark condenser for 3-4 hours. After cooling to room temperature, the solution was washed with 5% NaOH solution (2×20 ml), then with water (2×20 ml). The solution was then dried over anhydrous Na2SO4. The solvent was then removed under vacuum. The crude product, 4-benzhydryloxy-piperidine was obtained (2.46 g, 92.0% yield). 1H-NMR (CDCl3, ppm): 7.10-7.25 (m, 10H), 5.41 (s, 1H), 3.48 (m, 1H), 3.13 (m, 2H), 2.78 (m, 2), 1.86 (m, 2H), 1.66 (m, 2H). ESMS 268.1 (M+1), 290.1 (M+23).

Workup

  1. temperatureThe mixture was refluxed with a Dean-Stark condenser for 3-4 hours
  2. washthe solution was washed with 5% NaOH solution (2×20 ml)
  3. dry with materialThe solution was then dried over anhydrous Na2SO4
  4. customThe solvent was then removed under vacuum

Sources & evidence

ORD record
ord-db9da986dbd04572a211abec1f2ae774
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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