Hydrogen chloride-ethyl acetate → 8-(1-Cyclopentylethoxy)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine hydrochloride

HRID 2191295Notes

Reaction equation

HRID 2191295 reaction equation
[CH:1]1([CH:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH2:16][O:17][C:18]=3[N:19]=2)[CH3:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:27].C(OCC)(=O)C>>[ClH:27].[CH:1]1([CH:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:13][NH:14][CH2:15][CH2:16][O:17][C:18]=3[N:19]=2)[CH3:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68427277HCID 68427277, compound

Product 1

HCID 684293708-(1-Cyclopentylethoxy)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine hydrochlorideYield 71%

Procedure

A mixture of the compound obtained in step 1 (0.42 g) and 4N hydrogen chloride/ethyl acetate (3 mL) was stirred at room temperature for 3 hr. The precipitate was collected by filtration, and recrystallized from ethanol-diisopropyl ether to give the title compound (0.24 g, 71%) as a white powder. 1H-NMR (DMSO-d6): δ1.22 (3H, t, J=8.1 Hz), 1.20-1.40 (2H, m), 1.48-1.65 (4H, m), 1.65-1.80 (2H, m), 2.00-2.35 (1H, m), 3.46 (2H, brs), 4.23-4.34 (4H, m), 4.85-5.00 (1H, m), 6.54 (1H, d, J=8.2 Hz), 7.75 (1H, d, J=8.2 Hz), 9.59 (2H, brs)

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customrecrystallized from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-31ada8b544dd48929100c0dee8c078b5
Source dataset
uspto-grants-2012_12
Patent number
US08329687B2

Reaction notes

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