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ChemicalBook CAS DataBase List Loratadine Impurity 17
133330-72-0

Loratadine Impurity 17 synthesis

1synthesis methods
31251-41-9 Synthesis
8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one

31251-41-9
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Loratadine Impurity 17

133330-72-0
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Yield: 100%

Reaction Conditions:

Stage #1:8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one with sodium tetrahydroborate in methanol at 0 - 20; for 1 h;
Stage #2: with hydrogenchloride in methanol;water

Steps:

3.E
The title compound of Step D (700 mg) above was dissolved in MeOH (10 ml) and cooled to 00C. NaBH4 (95 mg) was added in one portion. The mixture was allowed to warm to RT and stirred for 1 h. The reaction was acidified with 1 N HCl and subsequently, brought to pH 12 with 1 N NaOH. The mixture was poured in water (100 ml) and extracted with CHCl3 (100 ml). The organic phase was dried over MgSO4 and concentrated affording the title compound (705 mg; 100 %).1HNMR δ (MeOD-dO 3.0-3,4 (m, 4H), 6.1(s, IH), 7.1.7.3 (m, 3H), 7.5-7.6 (m, 2H), 8.3:8.4 (m, IH)

References:

ALANTOS PHARMACEUTICALS, INC. WO2006/116157, 2006, A2 Location in patent:Page/Page column 56; 58

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