Sodium Bicarbonate → 1-Benzoyl-3-[2-[4-(benzothiazol-2-yl)-piperidin-1-yl]-ethyl]-3-(3,4-dimethoxy-phenyl)-pyrrolidine

HRID 2269840Notes

Reaction equation

HRID 2269840 reaction equation
[C:1]([N:9]1[CH2:13][CH2:12][C:11]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)([CH2:14][CH2:15]S(C)(=O)=O)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[CH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.CO>O1CCCC1.O.ClCCl>[C:1]([N:9]1[CH2:13][CH2:12][C:11]([CH2:14][CH2:15][N:42]2[CH2:43][CH2:44][CH:39]([C:31]3[S:30][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[N:32]=3)[CH2:40][CH2:41]2)([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 14774392-(Piperidin-4-yl)-1,3-benzothiazoleHCID 155428841-Benzoyl-3-(3,4-dimethoxy-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidineHCID 21584119Ethylacetate methanol

Product 1

HCID 101876901-Benzoyl-3-[2-[4-(benzothiazol-2-yl)-piperidin-1-yl]-ethyl]-3-(3,4-dimethoxy-phenyl)-pyrrolidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Combine 1-benzoyl-3-(3,4-dimethoxy-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.63 g, 1.45 mmol) and 4-(benzothiazol-2-yl)-piperidine (0.35 g, 1.60 mmol), and sodium bicarbonate (0.24 g, 2.9 mmol) in tetrahydrofuran/water (15/4) (30 mL). Heat to reflux. After 48 hours, cool to ambient temperature and evaporate in vacuo to obtain a residue. Partition the residue between dichloromethane and 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 5/1 ethyl acetate/methanol to give a solid. Combine the solid with dichloromethane and extract with 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Dry the residue in vacuo at 65° C. to give the title compound: Rf=0.24 (silica gel, 5/1 ethyl acetate/methanol); mp; 60-62° C. Elemental Analysis calculated for C33H37N3O3S·0.25 H1O: C 70.75; H 6.75; N 7.50; Found: C 70.79; H 6.70; N 7.39.

Workup

  1. temperatureHeat to reflux
  2. customevaporate in vacuo
  3. customto obtain a residue
  4. customPartition the residue between dichloromethane and 5% sodium bicarbonate solution
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto obtain a residue
  9. extractionextract with 5% sodium bicarbonate solution
  10. dry with materialDry the organic layer over Na2SO4
  11. filtrationfilter
  12. concentrationconcentrate in vacuo
  13. customto obtain a residue
  14. customDry the residue in vacuo at 65° C.

Sources & evidence

ORD record
ord-a26b4e4af5fa4fc9a7202857cbe73e58
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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