Benzhydrol → 4-((Diphenylmethoxy)methyl)piperidine

HRID 1383455Notes

Reaction equation

HRID 1383455 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.[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21]O)[CH2:17][CH2:16]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:2]1([CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:14][CH2:21][CH:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7037BenzhydrolHCID 4207714-PiperidinemethanolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 27624204-((Diphenylmethoxy)methyl)piperidineYield 82.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a round bottom flask, benzhydrol (1.84 g, 10 mmol, 1.0 eq.), piperidin-4-yl-methanol (1.15 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-(1,1-diphenyl-methoxymethyl)-piperidine was obtained (2.33 g, 82.8% yield). 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-2eee3e6e455e4747845553a961fdba24
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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