Acetic Acid → Tedatioxetine Hydrobromide

HRID 628780Notes

Reaction equation

HRID 628780 reaction equation
[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]2[CH2:19][CH2:18][N:17](C(OCC)=O)[CH2:16][CH2:15]2)=[CH:3][CH:2]=1.[BrH:26].C(O)(=O)C>>[BrH:26].[C:1]1([CH3:25])[CH:2]=[CH:3][C:4]([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 45258309Ethyl 4-(2-(4-tolylsulfanyl)phenyl)-piperidin-1-carboxylate

Product 1

HCID 24751582Tedatioxetine Hydrobromide

Conditions

Temperature
80 °C

Procedure

The crude ethyl 4-(2-(4-tolylsulfanyl)phenyl)-piperidin-1-carboxylate as a red oil from example 3 was mixed in a stirred reactor with hydrobromic acid in acetic acid (40%, 545 mL, 3.11 mol). The mixture was heated at 80° C. for 18 hours. The reaction mixture was cooled down to room temperature. During the cooling the product crystallises out. After 1 hour at room temperature ethyl ether (800 mL) was added to the reaction mixture, and the mixture was stirred for another hour. The product was filtered off, washed with ethyl ether and dried in a vacuum oven at 50° C. until constant weight.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. customDuring the cooling the product crystallises out
  3. additionAfter 1 hour at room temperature ethyl ether (800 mL) was added to the reaction mixture
  4. filtrationThe product was filtered off
  5. washwashed with ethyl ether
  6. customdried in a vacuum oven at 50° C. until constant weight

Sources & evidence

ORD record
ord-1a2043f2de5c4a1a9284636f2d4ea18b
Source dataset
uspto-grants-2016_04
Patent number
US09315459B2

Reaction notes

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