(S)-(+)-4-(oxiranylmethoxy)benzo[b]thiophene → 4-(3-Ethylbenzo[b]thiophen-2-yl)piperidine

HRID 1837484Notes

Reaction equation

HRID 1837484 reaction equation
O[C:2]1([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[C:9]=2[CH2:17][CH3:18])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.O1C[C@H]1COC1C2C=CSC=2C=CC=1>CO>[CH2:17]([C:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[S:12][C:8]=1[CH:2]1[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]1)[CH3:18]

Participants

4

Reactant 2

HCID 12992768(S)-(+)-4-(oxiranylmethoxy)benzo[b]thiopheneHCID 225958794-Hydroxy-4-(3-ethylbenzo[b]thiophen-2-yl)piperidine

Product 1

HCID 129927724-(3-Ethylbenzo[b]thiophen-2-yl)piperidineYield 72.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution 4-hydroxy-4-(3-ethylbenzo[b]thiophen-2-yl)piperidine (0.069 g, 0.281 mmol) and (S)-(+)-4-(oxiranylmethoxy)-benzo[b]thiophene (0.058 g, 0.281 mmol) in methanol (3 mL) was heated at reflux for 18 hours and then cooled and evaporated. The residue was purified using silica gel chromatography (dichloromethane/1% methanol in dichloromethane) to give the free base of the final title compound as a clear colorless oil (0.050 g, 39%). The oxalate salt was prepared to give the title compound. FDMS m/e=452 (M++1 of free base). C26H29NO2S2.C2H2O4

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. customevaporated
  4. customThe residue was purified

Sources & evidence

ORD record
ord-753e633333904d5b9a89d4df7d0f37da
Source dataset
uspto-grants-2004_08
Patent number
US06784180B2

Reaction notes

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