Ethyl chloroformate → 4-Indol-1-yl-piperidine-1-carboxylic acid ethyl ester

HRID 1378520Notes

Reaction equation

HRID 1378520 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(Cl)Cl>[CH2:27]([O:26][C:24]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)[CH2:10][CH2:9]1)=[O:25])[CH3:28]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 212222251-Benzyl-4-(1-indolyl)-piperidine

Product 1

HCID 140907494-Indol-1-yl-piperidine-1-carboxylic acid ethyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-N-(1-benzyl-piperidin-4-yl)-indole (100 g, 0.344 mol) in methylene chloride (1 L) was added ethyl chloroformate (99.2 mL) dropwise with stirring. The mixture was refluxed for 48 hours, cooled to room temperature, and concentrated. The residue was crystallized from i-propanol to give the title compound as colorless crystals (50 g, 53% yield). M.Pt.: 127° C.

Workup

  1. temperatureThe mixture was refluxed for 48 hours
  2. concentrationconcentrated
  3. customThe residue was crystallized from i-propanol

Sources & evidence

ORD record
ord-f170bc2b096f4c4a8bfda74f8ea4d2cb
Source dataset
uspto-grants-1997_09
Patent number
US05668152

Reaction notes

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