Oxalic Acid → HCID 86750000, compound

HRID 1779615Notes

Reaction equation

HRID 1779615 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]2[CH:8]=[CH:9][NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1.[O:15]=[C:16]1[C:25]2([CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[C:37]([OH:42])(=[O:41])[C:38]([OH:40])=[O:39]>C(#N)C.C(OCC)(=O)C>[C:37]([OH:42])(=[O:41])[C:38]([OH:40])=[O:39].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:28]3[CH2:27][CH2:26][C:25]4([C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH2:18][CH2:17][C:16]4=[O:15])[CH2:30][CH2:29]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 11430Potassium CarbonateHCID 116941694-(3-chloropropoxy)-1H-indoleHCID 212683293,4-Dihydrospiro[naphthalene-1(2H),4′-piperidin]-2-one

Product 1

HCID 86750000HCID 86750000, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 1-chloro-3-(1H-indole-4-oxy)propane, 3,4-dihydro-2-oxospiro[naphthalene-1(2H),4'-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 37% overall yield. FDMS m/e=388 (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-3a38497b263e41ec8bcd292b2bb5c9d9
Source dataset
uspto-grants-1997_05
Patent number
US05627196

Reaction notes

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