Butyl iodide → 1'-n-Butylspiro[indane-1,4'-piperidine]

HRID 1587680Notes

Reaction equation

HRID 1587680 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](I)[CH2:22][CH2:23][CH3:24]>CN(C=O)C>[CH2:21]([N:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 156376162,3-Dihydrospiro(indene-1,4'-piperidine)

Product 1

HCID 151631621'-n-Butylspiro[indane-1,4'-piperidine]Yield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In the same way as that described in Example 1, step 5, the title compound was prepared using spiro[indane-1,4'-piperidine] (77 mg, 0.41 mmol), DMF (10 ml), potassium carbonate (68 mg, 0.49 mmol), and n-butyl iodide (0.05 ml, 0.45 mmol). The crude residue was chromatographed using 5:95 methanol: dichloromethane, to give 1'-n-butylspiro[indane-1,4'-piperidine] (53 mg, 53%) as a beige solid.

Workup

  1. customThe crude residue was chromatographed

Sources & evidence

ORD record
ord-09438b97f4db4966836ae4b307a76850
Source dataset
uspto-grants-1993_06
Patent number
US05219860

Reaction notes

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