Trityl chloride → HCID 57164649, compound

HRID 1380903Notes

Reaction equation

HRID 1380903 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(N(CC)CC)C.[C:19]1([C:25](Cl)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[NH:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH:8]([C:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH3:9])=[O:6])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 57164649HCID 57164649, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred, ice-cooled, solution of ethyl isonipecotate (78.5 g, 0.50 mole) and triethylamine (200 ml, 1.4 mole) in CHCl3 (1000 ml), triphenylmethyl chloride (15.33 g, 0.55 mole) was added. After stirring overnight at room temperature, the reaction mixture was washed with H2O, dried (Na2SO4) and the solvent evaporated. The oily residue was crystallized from MeOH-CHCl3, yielding 108.19 (96 percent) of 4-piperidine carboxylic acid, 1-(triphenylmethyl)ethyl ester as a white solid; mp 154°-155° C.

Workup

  1. temperatureTo a stirred, ice-cooled
  2. washthe reaction mixture was washed with H2O
  3. dry with materialdried (Na2SO4)
  4. customthe solvent evaporated
  5. customThe oily residue was crystallized from MeOH-CHCl3

Sources & evidence

ORD record
ord-9cafeba51ac547939e5d0d2cdd18e9b5
Source dataset
uspto-grants-1986_04
Patent number
US04584301

Reaction notes

Loading…