Potassium Carbonate → HCID 86584242, compound

HRID 2288212Notes

Reaction equation

HRID 2288212 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14]/[CH:15]=[CH:16]/[CH2:17][Cl:18])[CH2:10][C@H:9]1[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)=[O:7].[NH:39]1[CH2:44][CH2:43][S:42][CH2:41][CH2:40]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[ClH:18].[ClH:18].[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14]/[CH:15]=[CH:16]/[CH2:17][N:39]2[CH2:44][CH2:43][S:42][CH2:41][CH2:40]2)[CH2:10][C@H:9]1[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 67164Thiomorpholine2×HCID 86584244HCID 86584244, compound

Product 1

HCID 86584242HCID 86584242, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[(E)-4-chloro-2-butenyl]-2-(2-naphthylmethyl)piperazine (300 mg), thiomorpholine (0.054 ml) and powdered potassium carbonate (100 mg) in dry acetonitrile (3 ml) was heated at 50° C. for 10 hours. Additional potassium carbonate (100 mg) and thiomorpholine (0.054 ml) were added and then the resulting mixture was further heated at the same temperature. After 2 hours, the reaction mixture was cooled and then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol (40:1). The obtained product was dissolved in ethyl acetate and treated with 4N hydrogen chloride in ethyl acetate (0.6 ml) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(2-naphthylmethyl)-4-((E)-4-thiomorpholino-2-butenyl)piperazine dihydrochloride (190 mg).

Workup

  1. temperaturethe resulting mixture was further heated at the same temperature
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by column chromatography on silica gel using
  6. additiona mixture of dichloromethane and methanol (40:1)
  7. dissolutionThe obtained product was dissolved in ethyl acetate
  8. additiontreated with 4N hydrogen chloride in ethyl acetate (0.6 ml)

Sources & evidence

ORD record
ord-e0a953a0d27244a19223686cbb530dae
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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