Sodium Iodide → 2-(3-Cyano-3,3-diphenylpropyl)-1-(3,4-methylenedioxyphenethyl)piperidine

HRID 974965Notes

Reaction equation

HRID 974965 reaction equation
[C:1]([C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1)#[N:2].[CH2:24]1[O:35][C:34]2[CH:33]=[CH:32][C:28]([CH2:29][CH2:30]Br)=[CH:27][C:26]=2[O:25]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.C(OCC)(=O)C.O>[C:1]([C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[CH2:30][CH2:29][C:28]1[CH:32]=[CH:33][C:34]2[O:35][CH2:24][O:25][C:26]=2[CH:27]=1)#[N:2]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 122072243,4-Methylenedioxyphenethyl bromideHCID 199701912-(3-Cyano-3,3-diphenylpropyl)piperidine

Product 1

HCID 199701872-(3-Cyano-3,3-diphenylpropyl)-1-(3,4-methylenedioxyphenethyl)piperidineYield 9.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(3-cyano-3,3-diphenylpropyl)piperidine (217 mg, 0.74 mmol--see Preparation 18), 3,4-methylenedioxyphenethyl bromide (186 mg, 0.82 mmol--see Preparation 12), potassium carbonate (1.0 g) and sodium iodide (20 mg) in acetonitrile (10 ml) was heated under reflux for 48 hours, allowed to cool to room temperature and diluted with ethyl acetate and water. The organic layer was dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-5% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (31 mg, 9%) as a colourless oil, which was characterised as containing 0.75 of an equivalent of water.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by chromatography on silica
  6. customevaporated

Sources & evidence

ORD record
ord-e25de71c0b26490493a691aea975216d
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

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