3-Chlorobenzoic Acid → Loratadine N-oxide

HRID 861739Notes

Reaction equation

HRID 861739 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:27]=1.ClC1C=C(C=CC=1)C(O)=[O:33]>ClCl.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:17][CH2:18][N:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][CH2:21]3)[C:10]3=[N+:11]([O-:33])[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:27]=1

Participants

5

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 3957Loratadine

Product 1

HCID 29982763Loratadine N-oxideYield 51.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24526ChlorineSolvent

Procedure

8-chloro-11-(1-ethoxycarbonyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (5 g, 13.06 mmol) was dissolved in CH2 Cl2 at -10° C. 3-Chlorobenzoic acid (4.9 g, 15.67 mmol) was then added and the reaction mixture stirred for 95 minutes. The reaction mixture was taken up in CH2Cl2 and extracted with sodium bisulfite, 10% NaOH. The crude reaction product was purified on silica gel eluting first with 1% and then with 2% MeOH in CH2Cl2 to give the title compound (2.7 g, MH+ 399).

Workup

  1. extractionextracted with sodium bisulfite, 10% NaOH
  2. customThe crude reaction product
  3. customwas purified on silica gel eluting first with 1%

Sources & evidence

ORD record
ord-9f958386efa44995a6b1bb171a1f4152
Source dataset
uspto-grants-1998_02
Patent number
US05714609

Reaction notes

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