Ethyl chloroformate → Deschloro Loratadine

HRID 223460Notes

Reaction equation

HRID 223460 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].C[N:8]1[CH2:13][CH2:12][C:11](=[C:14]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH2:18][CH2:17][C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]2=3)[CH2:10][CH2:9]1>C1C=CC=CC=1>[C:4]([N:8]1[CH2:9][CH2:10][C:11](=[C:14]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH2:18][CH2:17][C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]2=3)[CH2:12][CH2:13]1)([O:3][CH2:1][CH3:2])=[O:5]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 19861Azatadine

Product 1

HCID 12884174Deschloro Loratadine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 10.9 g (0.1 mole) of ethylchloroformate in 300 ml of anhydrous benzene is added dropwise, with stirring at room temperature, a solution of 14.5 g (0.05 M) of 11-(N-methyl-4-piperidylidene)-6,11-dihydro-5H-benzo-[5,6]-cyclohepta-[1,2-b]-pyridine (hereinafter referred to as Compound IA) in 200 ml of benzene. The solution is stirred and is heated under reflux overnight (16-20 hrs.). The mixture is cooled and is poured into ice water and the organic layer is separated, washed with water, dried, and then concentrated to dryness. The residue is triturated with petroleum ether and a white solid having a melting point of 106°-107° C. is recrystallized from isopropyl ether after decolorization with decolorizing carbon.

Workup

  1. stirringThe solution is stirred
  2. temperatureis heated
  3. temperatureunder reflux overnight (16-20 hrs.)
  4. temperatureThe mixture is cooled
  5. customthe organic layer is separated
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated to dryness
  9. customThe residue is triturated with petroleum ether
  10. customis recrystallized from isopropyl ether after decolorization with decolorizing carbon

Sources & evidence

ORD record
ord-7c279a44c98f414fb0971a8ea9f2cfee
Source dataset
uspto-grants-1982_10
Patent number
US04355036

Reaction notes

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