Trifluoroacetic acid → 4-[2-(Methylsulfanyl)phenyl]piperidine

HRID 2256048Notes

Reaction equation

HRID 2256048 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][CH3:24])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C1(SC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH3:24][S:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 111106201-Benzyloxycarbonyl-4(2-methylthiophenyl)piperidine

Product 1

HCID 190291654-[2-(Methylsulfanyl)phenyl]piperidineYield 63%

Conditions

Temperature
60 °C

Procedure

A mixture of 1-benzyloxycarbonyl-4-(2-methylthiophenyl)piperidine (0.34 g) and thioanisole (0.58 mL) was treated with trifluoroacetic acid (5 mL) and the mixture was heated to 60° C. for 30 minutes. At the end of this period, the reaction mixture was evaporated and diluted with ether. Extraction with water, neutralization of the aqueous layer with sodium bicarbonate and extraction with ethyl acetate afforded the crude product. This material was purified by column chromatography; elution with 19:1 dichloromethane:methanol containing 5% triethylamine afforded the named product (0.13 g); MS: 208 (M+1): NMR: 1.4-1.8 (q, d, J1 =25, J2 =12, 2), 1.8-1.9 (m, 2), 2.46 (s, 3), 2.8-2.9 (d, t, J1 =12, J2 =2.7, 2), 3.1-3.2 (m, 1), 3.3 (br, 2), 4.0 (br, 1), 7.1-7.3 (m, 4).

Workup

  1. customAt the end of this period, the reaction mixture was evaporated
  2. additiondiluted with ether
  3. extractionExtraction with water, neutralization of the aqueous layer
  4. extractionwith sodium bicarbonate and extraction with ethyl acetate
  5. customafforded the crude product
  6. customThis material was purified by column chromatography
  7. washelution with 19:1 dichloromethane

Sources & evidence

ORD record
ord-5694831843f54c1393b287ddad6a7c33
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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