Potassium Carbonate → HCID 9817776, compound

HRID 1941460Notes

Reaction equation

HRID 1941460 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1.[CH:18]1([C:21](Cl)=[O:22])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].[K+].[Br-]>C(#N)C>[CH:18]1([C:21]([N:15]2[CH2:16][CH2:17][CH:12]([CH:9]3[C:10]4[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=4)[CH2:7][CH2:8]3)[CH2:13][CH2:14]2)=[O:22])[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 77637Cyclopropanecarbonyl chlorideHCID 253877Potassium BromideHCID 21461148HCID 21461148, compound

Product 1

HCID 9817776HCID 9817776, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(6-methoxy-indan-1-yl)piperidine (0.46 g, 2 mmol), cyclopropane carbonyl chloride (0.21 g, 2 mmol), and excess powdered potassium carbonate in acetonitrile was stirred for 72 h. The solution was filtered and concentrated in vacuo. The residue chromatographed on silica eluting with 2% methanol in methylene chloride to give, on concentration of the appropriate fractions, the product as an oil (0.5 g, 83%), IR (KBr) 2940, 1636, 1490, 1244, 1034 cm-1 ; H NMR (CDCl3, 300 MHz) δ 7.08 (d, 1H, J=7.9 Hz), 6.70-6.67 (m, 2H), 5.27 (m, 2H), 3.77 (s, 3H), 3.10-3.04 (m, 1H), 2.83-2.67 (m, 4H), 2.13-2.03 (m, 1H), 1.92-1.83 (m, 2H), 1.75-1.67 (m, 2H), 1.52-1.48 (m, 1H), 1.37-1.18 (m, 2H), 0.96-0.91 (m,2H). 0.73-0.67 (m, 2H). Anal. Calc'd for C19H25 NO2 ·0.2CH2Cl2 : C, 73.08%; H, 8.03%; N, 4.39%. Found: C, 72.81%; H, 7.94%; N, 4.44%.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue chromatographed on silica eluting with 2% methanol in methylene chloride
  4. customto give, on concentration of the appropriate fractions

Sources & evidence

ORD record
ord-cfc351cf1abc4df18e206e7ba534405a
Source dataset
uspto-grants-1997_12
Patent number
US05703239

Reaction notes

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