Chloroform → HCID 15700343, compound

HRID 377267Notes

Reaction equation

HRID 377267 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[N:13]1([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C.C(Cl)(Cl)Cl>C1C=CC=CC=1>[N:13]1([CH:18]2[CH2:23][CH2:22][N:21]([C:2]([Cl:1])=[O:4])[CH2:20][CH2:19]2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 787034-(1-Pyrrolidinyl)piperidineHCID 94429Triphosgene

Product 1

HCID 15700343HCID 15700343, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Triphosgene (742 mg, 2.5 mmol) was dissolved in benzene (60 ml), followed by the addition of a solution of 4-pyrrolidinopiperidine (1.00 g, 6.5 mmol) in benzene and triethylamine (7.5 mmol). The resulting mixture was stirred at room temperature for 17 hours. Chloroform was added to the reaction mixture, and the thus-obtained mixture was washed with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (chloroform-acetone mixed solvent [1:2]), whereby 4-pyrrolidinopiperidinocarbonyl chloride (158 mg, 11%) was obtained.

Workup

  1. washthe thus-obtained mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column (chloroform-acetone mixed solvent [1:2])

Sources & evidence

ORD record
ord-4923eb6714e04e54a3ce7bb0c3f87d05
Source dataset
uspto-grants-2000_02
Patent number
US06025385

Reaction notes

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