Hydrochloric Acid → HCID 78145359, compound

HRID 717899Notes

Reaction equation

HRID 717899 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[O:5][C:6]1[CH:15]=[CH:14][C:13]2[NH:12][CH:11]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:10]3[CH2:22][CH2:23][CH2:24][O:25][CH:9]3[C:8]=2[CH:7]=1.Cl>CC(C)=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[O:5][C:6]1[CH:15]=[CH:14][C:13]2[NH:12][CH:11]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[CH:10]3[CH2:22][CH2:23][CH2:24][O:25][CH:9]3[C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 78139891HCID 78139891, compound

Product 1

HCID 78145359HCID 78145359, compoundYield 158.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To an ice-cooed solution of (4aSR*,5SR*,10bSR*)-9-(3-chlorophenoxy)-5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline (60 mg, 0.151 mmol) in acetone (500 μL) was added dropwise a 2 M HCl solution (in ether, 83 μL, 0.166 mmol, 1.1 equiv.). After 30 min. stirring at r.t., a solid had precipitated. The solid was filtered off and dried in vacuum to give (4aSR*,5SR*,10bSR*)-9-(3-chlorophenoxy)-5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline hydrochloride (52 mg, 79%) as white solid. (Example 2).

Workup

  1. customa solid had precipitated
  2. filtrationThe solid was filtered off
  3. customdried in vacuum

Sources & evidence

ORD record
ord-0754933c0d494bb3b99a5277bcb1dda3
Source dataset
uspto-grants-2015_11
Patent number
US09193738B2

Reaction notes

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