Sodium Iodide → 4-Phenyl-1-(2-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)ethyl)piperidine

HRID 1516939Notes

Reaction equation

HRID 1516939 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[C:12]2[CH:11]=[CH:10][S:9][C:8]=2[CH2:7][CH2:6][CH2:5]1.Cl.[C:14]1([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[C:14]1([CH:20]2[CH2:21][CH2:22][N:23]([CH2:2][CH2:3][CH:4]3[C:12]4[CH:11]=[CH:10][S:9][C:8]=4[CH2:7][CH2:6][CH2:5]3)[CH2:24][CH2:25]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 825094-Phenylpiperidinium chlorideHCID 578554434-(2-Chloroethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene

Product 1

HCID 249834684-Phenyl-1-(2-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)ethyl)piperidineYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2-chloroethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene (0.25 g, 1.24 mmol), 4-phenylpiperidine hydrochloride (0.25 g, 1.25 mmol), K2CO3 (0.40 g, 2.89 mmol) and a catalytic amount of NaI in DMF (5 mL) is heated to 110° C. overnight. The solvent is removed at reduced pressure, diethyl ether is added to the residue and washed with water. The organic phase is dried and evaporated at reduced pressure and the resulting crude is purified by column chromatography, giving 4-phenyl-1-(2-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)ethyl)piperidine (0.24 g, 0.74 mmol, 59%, oil). 1H NMR (300 MHz, CDCl3): δ1.54 (m, 1H), 1.70-2.18 (m, 11H), 2.51 (m, 3H), 2.76 (m, 3H), 3.12 (m, 2H), 6.88 (d, J=5.2 Hz, 1H), 7.04 (d, J=5.2 Hz, 1H), 7.18-7.32 (m, 5H).

Workup

  1. customThe solvent is removed at reduced pressure, diethyl ether
  2. additionis added to the residue
  3. washwashed with water
  4. customThe organic phase is dried
  5. customevaporated at reduced pressure
  6. customthe resulting crude is purified by column chromatography

Sources & evidence

ORD record
ord-66767702d39d422da04a1dbc7afb68a2
Source dataset
uspto-grants-2012_07
Patent number
US08227625B2

Reaction notes

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