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Oxalic Acid → 1-(4-Indolyloxy)-2-(4-(2-naphthyl)piperidin-1-yl)ethane ethanedioate

HRID 565509
Notes
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Reaction equation

HRID 565509 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38]>C(#N)C.C(OCC)(=O)C>[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[NH:9]1[C:10]2[C:6](=[C:5]([O:4][CH2:3][CH2:2][N:27]3[CH2:28][CH2:29][CH:24]([C:15]4[CH:16]=[CH:17][C:18]5[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=5)[CH:14]=4)[CH2:25][CH2:26]3)[CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 11430Potassium CarbonateHCID 106317214-(2-chloroethoxy)-1H-indoleHCID 220292644-(Naphthalen-2-yl)piperidine

Product 1

HCID 867500051-(4-Indolyloxy)-2-(4-(2-naphthyl)piperidin-1-yl)ethane ethanedioate

Reagents, catalysts & solvents 2

HCID 6342
Acetonitrile
Solvent
HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 1-chloro-2-(4-indolyloxy)ethane, 4-(2-naphthyl)piperidine and 3 equivalents of potassium carbonate in acetonitrile was heated at reflux for 12 h. The mixture was cooled, diluted with ethyl acetate, and the organic layer was separated and washed with brine. The crude residue was purified by silica gel chromatography (dichloromethane/5% methanol in dichloromethane gradient eluent). The resulting free base was dissolved in ethyl acetate and precipitated with one equivalent of oxalic acid in ethyl acetate, to give the title compound in 29% overall yield as a white solid. mp. 119-120° C. FDMS m/e=370 (M+ of free base).

Workup

  1. temperatureat reflux for 12 h
  2. temperatureThe mixture was cooled
  3. customthe organic layer was separated
  4. washwashed with brine
  5. customThe crude residue was purified by silica gel chromatography (dichloromethane/5% methanol in dichloromethane gradient eluent)
  6. dissolutionThe resulting free base was dissolved in ethyl acetate

Sources & evidence

ORD record
ord-346ae427f474489389e65675df8afd5c
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06172073B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes