3-Chlorobenzoic Acid → Loratadine N-oxide

HRID 840271Notes

Reaction equation

HRID 840271 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]>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

4

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 3957Loratadine

Product 1

HCID 29982763Loratadine N-oxideYield 51.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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 CH2Cl2 at −10C. 3-Chlorobenzoic acid (4.9 g, 15.67 mmmol) 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-f92f31d293d9453db069630ef2e18263
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

Loading…