Trityl chloride → 3-Piperidinol, 1-(triphenylmethyl)-

HRID 1272379Notes

Reaction equation

HRID 1272379 reaction equation
Cl.[OH:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[OH:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 2723962Piperidine-3-ol hydrochloride

Product 1

HCID 222535813-Piperidinol, 1-(triphenylmethyl)-Yield 112.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 1.37 g (10.0 mmol) of 3-hydroxypiperidine hydrochloride and 2.53 g (3.5 mL) of triethylamine in 30 mL of dichloromethane at 0° C. was added dropwise 2.93 g (10.5 mmol) of trityl chloride. The mixture was stirred at ambient temperature overnight, diluted with 100 mL of dichloromethane, washed sequentially with water, 5% aqueous citric acid solution, saturated sodium bicarbonate solution, and brine, dried over sodium sulfate, and concentrated to give 3.85 g of the title compound as a white foam.

Workup

  1. washwashed sequentially with water, 5% aqueous citric acid solution, saturated sodium bicarbonate solution, and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3a4f1e0fdbb1471cbb779a997a789270
Source dataset
uspto-grants-2007_04
Patent number
US07208498B2

Reaction notes

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