Trityl chloride → HCID 22253565, compound

HRID 1250727Notes

Reaction equation

HRID 1250727 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O.C(OCC)(=O)C>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

Product 1

HCID 22253565HCID 22253565, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7.18 g (71 mmol) of 4-hydroxypiperidine in 100 ml dimethylformamide are added first 19.6 g (142 mmol) of powdered potassium carbonate and then 19.8 9 (71 mmol) of tritylchloride. The mixture is stirred for 22 hours at ambient temperature, diluted with ethyl acetate to twice the volume, washed with water and saturated saline solution, dried with magnesium sulphate and concentrated by evaporation. The residue is recrystallised from ethyl acetate/petroleum ether (1:4, v:v). 17.65 g (72.4% of theory) of 4-hydroxy-N-tritylpiperidine are obtained as colourless crystals, melting point 157-158° C.

Workup

  1. washwashed with water and saturated saline solution
  2. dry with materialdried with magnesium sulphate
  3. concentrationconcentrated by evaporation
  4. customThe residue is recrystallised from ethyl acetate/petroleum ether (1:4, v:v)

Sources & evidence

ORD record
ord-38f2998a7c1a42a693c10338d1748547
Source dataset
uspto-grants-2002_01
Patent number
US06339096B1

Reaction notes

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