Sodium Hydroxide → HCID 24860289, compound

HRID 1692606Notes

Reaction equation

HRID 1692606 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14][CH2:15][O:16][C:17]=2[N:18]=1.Cl.C(OCC)(=O)C.[OH-].[Na+]>>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][NH:13][CH2:14][CH2:15][O:16][C:17]=2[N:18]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 67280280HCID 67280280, compound

Product 1

HCID 24860289HCID 24860289, compoundYield 53.1%

Procedure

A mixture of the compound (0.09 g) obtained in step 1 and 4N hydrogen chloride/ethyl acetate (3 mL) was stirred at room temperature for 3 hr. An aqueous sodium hydroxide solution was added until the aqueous layer became alkaline. The organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (solvent gradient; 10→40% ethyl acetate/hexane) to give 8-(2-methylpiperidin-1-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.034 g, 52%) as a pale-yellow powder.

Workup

  1. washThe organic layer was washed with brine
  2. customdried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (solvent gradient; 10→40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4f82d120b70d4e60a7d46378425feb38
Source dataset
uspto-grants-2012_04
Patent number
US08158617B2

Reaction notes

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