Oxalic Acid → HCID 86750004, compound

HRID 1900976Notes

Reaction equation

HRID 1900976 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][NH:12]2.[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+].[C:39]([OH:44])(=[O:43])[C:40]([OH:42])=[O:41]>C(#N)C.C(OCC)(=O)C>[C:39]([OH:44])(=[O:43])[C:40]([OH:42])=[O:41].[NH:12]1[C:13]2[C:9](=[C:8]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:30]3[CH2:31][CH2:32][CH:27]([C:18]4[CH:19]=[CH:20][C:21]5[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH:17]=4)[CH2:28][CH2:29]3)[CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11]1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 11430Potassium CarbonateHCID 11658745HCID 11658745, compoundHCID 220292644-(Naphthalen-2-yl)piperidine

Product 1

HCID 86750004HCID 86750004, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 1-chloro-5-(4-indolyloxy)pentane, 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 47% overall yield as a white solid. mp. 178°-180° C. FDMS m/e=412 (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-a15924fdb6564b69a856e4464c65b91b
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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