Triethylamine → HCID 21833772, compound

HRID 1741122Notes

Reaction equation

HRID 1741122 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]([CH3:13])[CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][CH:15]=1.[CH3:23][N:24]1[CH2:29][CH2:28][C:27]2([C:40]3[C:32](=[CH:33][C:34]4[CH2:35][CH2:36][NH:37][C:38]=4[CH:39]=3)[O:31][CH2:30]2)[CH2:26][CH2:25]1.C(N(CC)CC)C>S(Cl)(Cl)=O>[CH3:23][N:24]1[CH2:25][CH2:26][C:27]2([C:40]3[C:32](=[CH:33][C:34]4[CH2:35][CH2:36][N:37]([C:20]([C:17]5[CH:18]=[CH:19][C:14]([C:3]6[CH:4]=[CH:5][C:6]([C:8]7[N:9]([CH3:13])[CH:10]=[CH:11][N:12]=7)=[CH:7][C:2]=6[CH3:1])=[CH:15][CH:16]=5)=[O:22])[C:38]=4[CH:39]=3)[O:31][CH2:30]2)[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 106579521'-Methyl-6,7-dihydro-2H,5H-spiro[furo[2,3-f]indole-3,4'-piperidine]HCID 21833857HCID 21833857, compound

Product 1

HCID 21833772HCID 21833772, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

2'-Methyl-4'-(1-methylimidazol-2-yl)biphenyl-4-carboxylic acid (D90, 310 mg, 1.06 mmol) was heated at reflux in thionyl chloride (10 ml) for 30 minutes, cooled, evaporated in vacuo and the orange residue redissolved in dry THF (10 ml). 1'-Methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (D8, 260 mg, 1.06 mmol) and triethylamine (0.15 ml, 1.06 mmol) were added and the mixture stirred for 72 hours. The mixture was evaporated in vacuo, the residue partitioned between H2O and CHCl3 (4 times) and the organics combined, dried over Na2SO4, filtered and evaporated in vacuo. The residue was purified by flash silica-gel chromatography with 2% MeOH/CHCl3 as eluant to yield the title compound as a pale yellow gum (224 mg, 41%) which was converted to the hydrochloride salt.

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. dissolutionthe orange residue redissolved in dry THF (10 ml)
  4. customThe mixture was evaporated in vacuo
  5. customthe residue partitioned between H2O and CHCl3 (4 times)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by flash silica-gel chromatography with 2% MeOH/CHCl3 as eluant

Sources & evidence

ORD record
ord-7810af2514de4eed8e784d9572555278
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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