Hydrochloric Acid → HCID 86584235, compound

HRID 2288201Notes

Reaction equation

HRID 2288201 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16]OS(C)(=O)=O)[CH2:10][C@H:9]1[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)=[O:7].[NH:42]1[CH2:47][CH2:46][S:45][CH2:44][CH2:43]1.C(N(CC)CC)C.[ClH:55]>CO.C(OCC)(=O)C>[ClH:55].[ClH:55].[F:40][C:2]([F:41])([F:1])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:37])([F:39])[F:38])[CH:35]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:42]2[CH2:47][CH2:46][S:45][CH2:44][CH2:43]2)[CH2:10][C@H:9]1[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67164ThiomorpholineHCID 54226805HCID 54226805, compound

Product 1

HCID 86584235HCID 86584235, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(2-naphthylmethyl)-4-(3-methylsulfonyloxypropyl)piperazine (250 mg), thiomorpholine (43 mg) and triethylamine (46 mg) in dry methanol (5 ml) was refluxed for 2 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel using ethyl acetate as an eluent. The product obtained was dissolved in ethyl acetate and treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(2-naphthylmethyl)-4-(3-thiomorpholinopropyl)piperazine dihydrochloride (195 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by column chromatography on silica gel
  4. customThe product obtained

Sources & evidence

ORD record
ord-597690319b4b4d479595ba5061430f9c
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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