Phosgene → HCID 18328692, compound

HRID 1249754Notes

Reaction equation

HRID 1249754 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[C:11](Cl)([Cl:13])=[O:12]>C(Cl)Cl>[CH:1]1([C:11]([Cl:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 70461,2,3,4-Tetrahydroisoquinoline

Product 1

HCID 18328692HCID 18328692, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1,2,3,4-Tetrahydroisoquinoline (0.5 g, 3.76 mmol) was added to a cooled mixture of phosgene (5 ml of 20% phosgene in toluene solution, 9.4 mmol) in methylene chloride (5 ml) at 0° C. The mixture was stirred at 0° C. for 1 hour. The reaction mixture was evaporated in vacuo. The residue was suspended in ethyl ether, filtered and the eluents were condensed to give a pale pink oil. Purification by flash column chromatography (silica gel, 0-10% ethyl acetate/hexane) gave 0.586 g of the desired product. IR (film) 1735.3 cm−1.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. filtrationfiltered
  3. customcondensed
  4. customto give a pale pink oil
  5. customPurification by flash column chromatography (silica gel, 0-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f7cef0cb701e42dfabaccfb3721e9c4e
Source dataset
uspto-grants-2002_01
Patent number
US06335324B1

Reaction notes

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