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

HRID 453721
Notes
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Reaction equation

HRID 453721 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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): δ 1.54 (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-7e0868c35c5c4514baf696adc346398f
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492563B2

Reaction notes

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