Trityl chloride → 1-Tritylpiperidin-3-one

HRID 480561Notes

Reaction equation

HRID 480561 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([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.Cl.[NH:22]1[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH2:23]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([N:22]1[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH2:23]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([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

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 22707028Piperidin-3-one hydrochloride

Product 1

HCID 227070511-Tritylpiperidin-3-oneYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trityl chloride (13.1 g, 47.0 mmol) was added to a stirred suspension of 3-piperidone hydrochloride (5.79 g, 42.7 mmol) and triethylamine (14.9 ml, 107 mmol) in CH2Cl2 (100 ml) and the reaction was stirred for 16 h under N2 at room temperature. The resulting mixture was filtered and the filtrate washed sequentially with H2O and 5% aqueous citric acid, dried over MgSO4 and evaporated under reduced pressure. Trituration with pentane afforded the subtitle compound as a colourless solid (4.8 g, 33%). Rf 0.23 (CH2Cl2/pentane 2/3, v/v). 1H NMR (CDCl3) δ: 2.05 (2H, m), 2.35 (2H, m), 2.45 (2H, m), 2.85 (2H, s), 7.06-7.55 (15H, m).

Workup

  1. filtrationThe resulting mixture was filtered
  2. washthe filtrate washed sequentially with H2O and 5% aqueous citric acid
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d9b252cd1b9147ccb6b5f19ae947394e
Source dataset
uspto-grants-2003_11
Patent number
US06653302B2

Reaction notes

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