Trityl chloride → HCID 12851303, compound

HRID 1584801Notes

Reaction equation

HRID 1584801 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl.C(N(CC)CC)C>[CH2:8]([O:7][C:5]([CH:4]1[CH2:3][CH2:2][N:1]([C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:11][CH2:10]1)=[O:6])[CH3:9]

Participants

5

Reactant 2

HCID 6456Trityl chlorideHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 12851303HCID 12851303, compoundYield 112.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of ethyl isonipecotate (25 g; 0.165 mol) in dichloromethane (250 ml) and triethylamine (50 ml) was cooled in a water bath and triphenylmethyl chloride (48.7 g; 0.175 mol) was added portionwise. Shortly after the addition was completed a precipitate was formed. The mixture was stirred at room temperature for 24 h and the mixture was then washed with water, dried over sodium sulfate and evaporated to dryness to give a yellow oil (74.0 g). This oil was triturated with methanol to give the product as cream coloured crystals in 97% yield (61.9 g); m.p. 164° C.

Workup

  1. additionShortly after the addition
  2. customwas formed
  3. washthe mixture was then washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-63185bb358db4ec09eac980bf1a789da
Source dataset
uspto-grants-1999_08
Patent number
US05935974

Reaction notes

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