Benzyl chloroformate → HCID 54523591, compound

HRID 2301144Notes

Reaction equation

HRID 2301144 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[CH2:24]([O:31][C:32](Cl)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)(O)[O-].[K+]>ClCCl>[CH2:24]([O:31][C:32]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)[CH2:10][CH2:9]1)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516893Potassium BicarbonateHCID 1378330HCID 1378330, compound

Product 1

HCID 54523591HCID 54523591, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(1-Benzyl-piperidin-4-yl)-1,2,3,4-tetrahydroisoquinoline (280 mg, 0.90 mmol), benzyloxycarbonyl chloride (310 mg, 1.8 mmol) and potassium bicarbonate (230 mg, 2.3 mmol) were stirred at room temperature for 23 hours in dichloromethane (5 ml). The reaction solution was mixed with dichloromethane, washed with water and saturated brine and the dried with anhydrous sodium sulfate. The solvent was removed by evaporation from the organic layer under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 300 mg (0.86 mmol, 96% in yield) of the title compound.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialthe dried with anhydrous sodium sulfate
  3. customThe solvent was removed by evaporation from the organic layer under a reduced pressure
  4. customthe thus obtained material was separated
  5. custompurified by a silica gel column chromatography
  6. customto obtain

Sources & evidence

ORD record
ord-ed3000123a88487fa696eaf246604485
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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