1,4-Dioxane hydrochloride → (R)-1-(4-trifluoromethyl-benzenesulfonyl)-piperazine-2-carboxylic acid 3-fluoro-4-trifluoromethoxy-benzylamide hydrochloride

HRID 908625Notes

Reaction equation

HRID 908625 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C@@H:10]([C:27](=[O:42])[NH:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[C:32]([F:41])[CH:31]=2)[CH2:9]1)=O)(C)(C)C.[ClH:43].O1CCOCC1>O1CCOCC1>[ClH:43].[F:41][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][C:33]=1[O:36][C:37]([F:40])([F:38])[F:39])[CH2:29][NH:28][C:27]([C@H:10]1[CH2:9][NH:8][CH2:13][CH2:12][N:11]1[S:14]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)(=[O:15])=[O:16])=[O:42]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59703799(R)-3-(3-fluoro-4-trifluoromethoxy-benzylcarbamoyl)-4-(4-trifluoromethyl-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86619482(R)-1-(4-trifluoromethyl-benzenesulfonyl)-piperazine-2-carboxylic acid 3-fluoro-4-trifluoromethoxy-benzylamide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the compound (60 mg) obtained in Step 4 in 1,4-dioxane (0.6 ml) was added 4N hydrogen chloride/1,4-dioxane solution (0.6 ml) with stirring at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated under reduced pressure. Toluene was added to the residue, and the mixture was concentrated again under reduced pressure to give a crude product (about 0.095 mmol) containing the title compound as a main component. The obtained crude product was directly used for the next reaction.

Workup

  1. stirringAfter stirring at room temperature for 2 days
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionToluene was added to the residue
  4. concentrationthe mixture was concentrated again under reduced pressure
  5. customto give a crude product (about 0.095 mmol)

Sources & evidence

ORD record
ord-3d49b9b5b47c4948876f19314de3dd18
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

Loading…