Triethylamine → HCID 9851614, compound

HRID 2288186Notes

Reaction equation

HRID 2288186 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=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[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:7].[NH:41]1[CH2:46][CH2:45][S:44][CH2:43][CH2:42]1.C(N(CC)CC)C>C(#N)C>[F:38][C:35]([F:37])([F:36])[C:33]1[CH:32]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:40])[F:39])[CH:34]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:41]2[CH2:46][CH2:45][S:44][CH2:43][CH2:42]2)[CH2:10][C@H:9]1[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67164ThiomorpholineHCID 53774435HCID 53774435, compound

Product 1

HCID 9851614HCID 9851614, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(3-methylsulfonyloxypropyl)piperazine (0.2 g), thiomorpholine (0.042 g) and triethylamine (0.09 ml) in dry acetonitrile (2 ml) was stirred at 90° C. for 15 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel using ethyl acetate-methanol (10:1) as an eluent to give (2R)-1-(3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(3-thiomorpholinopropyl)piperazine. The product obtained was dissolved in ethanol and treated with 17.6% hydrogen chloride in ethanol solution to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(3-thiomorpholinopropyl)piperazine dihydrochloride (0.19 g) as a powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d8f78b11aa134b07ad1402dc39dd0c7e
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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