Ethyl chloroformate → HCID 10247636, compound

HRID 1383462Notes

Reaction equation

HRID 1383462 reaction equation
[CH:1]([S:14][CH:15]1[CH2:20][CH2:19][N:18](C)[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1(C)C=CC=CC=1>[CH2:26]([O:25][C:23]([N:18]1[CH2:19][CH2:20][CH:15]([S:14][CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:16][CH2:17]1)=[O:24])[CH3:27]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 14624167HCID 14624167, compound

Product 1

HCID 10247636HCID 10247636, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The solution of 4-benzhydrylsulfanyl-1-methyl-piperidine (350 mg, 1.18 mmol) and ethyl chloroformate (0.33 mL, 3.54 mmol, 3 eq.) in toluene (15 ml) was refluxed for 5 hrs. The solution was cooled to room temperature and then washed with diluted HCl (2.0 N, 2×5 mL). The solution was dried over anhydrous Na2SO4. The solvent was moved and the crude product 4-benzhydrylsulfanyl-piperidine-1-carboxylic acid ethyl ester was yielded (322 mg, 76.8% yield).

Workup

  1. washwashed with diluted HCl (2.0 N, 2×5 mL)
  2. dry with materialThe solution was dried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-6ea45d2b16524ebda43f0724469f447b
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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