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Acetic Acid → 7-(2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1-methyl-1,2,3,4-tetrahydroquinoline

HRID 494975
Notes
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Reaction equation

HRID 494975 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([CH2:11][CH2:12][C:13]3[CH:22]=[C:21]4[C:16]([CH2:17][CH2:18][CH2:19][NH:20]4)=[CH:15][C:14]=3[O:23][CH3:24])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C=O.[C:27]([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C.C(OCC)(=O)C>[O:4]1[C:5]2([CH2:6][CH2:7][N:8]([CH2:11][CH2:12][C:13]3[CH:22]=[C:21]4[C:16]([CH2:17][CH2:18][CH2:19][N:20]4[CH3:27])=[CH:15][C:14]=3[O:23][CH3:24])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 576829147-(2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1,2,3,4-tetrahydroquinoline

Product 1

HCID 576829257-(2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1-methyl-1,2,3,4-tetrahydroquinolineYield 49%

Reagents, catalysts & solvents

2
HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

196 mg of 7-(2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1,2,3,4tetrahydroquinoline was dissolved in 5 ml of acetonitrile. Thereafter, 1 ml of 37% formalin, 190 mg of sodium cyanoborohydride, and 0.15 ml acetic acid were added to the reaction solution, and the obtained mixture was then stirred at room temperature for 1 hour. Thereafter, the reaction solution was diluted with ethyl acetate, and then washed with a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate), so as to obtain 100 mg of the subject compound.

Workup

  1. washwashed with a saturated sodium bicarbonate aqueous solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9726a7185a6541129431eb6de158bcd9
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07538123B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes