Potassium Carbonate → HCID 69200293, compound

HRID 2251914Notes

Reaction equation

HRID 2251914 reaction equation
CS(O[C@H:6]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[CH2:7]1)(=O)=O.[Br:24][C:25]1[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=1[CH2:27][O:28][C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH2:31].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:19]1([C:16]2[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][N:8]3[CH2:9][CH2:10][C@@H:6]([NH:31][C:30]4[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=4[O:28][CH2:27][C:26]4[CH:36]=[CH:37][CH:38]=[CH:39][C:25]=4[Br:24])[CH2:7]3)=[CH:14][CH:15]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 112081902-(o-Bromobenzyloxy) anilineHCID 59643988(S)-3-methanesulfonyloxy-1-(4-pyrrolidinophenethyl)pyrrolidine

Product 1

HCID 69200293HCID 69200293, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

(S)-3-Methanesulfonyloxy-1-(4-pyrrolidinophenethyl)pyrrolidine (0.30 g, 0.89 mmol) was added to 2-(2-bromobenzyloxy)aniline (1.15 g, 4.13 mmol) in argon stream. The obtained mixture was dissolved in acetonitrile (50 ml). Potassium carbonate (1.62 g, 11.7 mmol) was added to the obtained solution, and they were refluxed for 85 hours. Acetonitrile (15 ml) was added to the reaction mixture, and they were refluxed for additional 48 hours. The reaction mixture was filtered through Celite to obtain the filtrate. The solvent was evaporated under reduced pressure to obtain the title compound in the form of a brown oily mixture (1.40 g).

Workup

  1. temperaturewere refluxed for 85 hours
  2. temperaturewere refluxed for additional 48 hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. customto obtain the filtrate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c502d0469d1446b08c33f2fa20d0e565
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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