Sodium Iodide → HCID 10781757, compound

HRID 1744204Notes

Reaction equation

HRID 1744204 reaction equation
[CH:1]1[C:5]2=[CH:6][S:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=[O:11])[N:4]2[CH2:3][CH:2]=1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[Na+].[Na+].[Na+].[I-]>CC#N>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C@H:6]2[C@@H:5]3[CH2:1][CH2:2][CH2:3][N:4]3[C:10](=[O:11])[C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[S:7]2)[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 531671-MethylpiperazineHCID 54416786HCID 54416786, compound

Product 1

HCID 10781757HCID 10781757, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (+)-11-chloro-2,3,11,11a-tetrahydro-1H,5H,-pyrrolo[2,1-c][1,4]benzothiazepin-5-one (38)15 (0.6 g, 2.4 mmol), freshly distilled 1-methylpiperazine (0.34 mL, 3.1 mmol), Na2CO3(1.06 g, 10.0 mmol), NaI (0.36 g, 2.4 mmol) in dry CH3CN (30 mL) was gently refluxed for 20 hours. The solvent was evaporated and the residue was partitioned between CH2Cl2 and water. The organic phase was successively washed with a 2% solution of Na2S2O3, water and brine. The residue obtained after evaporation was chromatographed on silica gel eluting with 5% methanol in CH2Cl2. The title compound 27 was obtained as a white solid (0.55 g, 73% yield): mp 188–190° C. (2-propanol-isopropyl ether); IR (KBr) 1630 cm−1; 1H NMR (CDCl3) δ7.71 (m, 1H), 7.50 (m, 2H), 7.61 (m, 1H), 7.33 (m, 2H), 4.36 (d, 1H, J=11.2 Hz), 3.70 (m, 3H), 2.58 (m, 4H), 2.38 (m, 4H), 2.27 (s, 3H), 2.02 (m, 4H). MS m/z 317 (100, M+), 217, 180, 139, 99, 70. Anal. (C17H23N3OS)C, H, N.

Workup

  1. additionA mixture of (+)-11-chloro-2,3,11,11a-tetrahydro-1H,5H
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between CH2Cl2 and water
  4. washThe organic phase was successively washed with a 2% solution of Na2S2O3, water and brine
  5. customThe residue obtained
  6. customafter evaporation
  7. customwas chromatographed on silica gel eluting with 5% methanol in CH2Cl2

Sources & evidence

ORD record
ord-9fc13c8d92864936a61fd3a275642a38
Source dataset
uspto-grants-2006_03
Patent number
US07015212B1

Reaction notes

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