Stannous chloride dihydrate → HCID 19769862, compound

HRID 1656590Notes

Reaction equation

HRID 1656590 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=3)=[O:18])[CH2:15][CH2:16]2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 19788719HCID 19788719, compound

Product 1

HCID 19769862HCID 19769862, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound of Example 1 (2.00 g, 4.47 mmol) and tin (II) chloride dihydrate (8.06 g, 35.75 mmol) were stirred together in ethanol (30 mL) at 70° C. for 6 hours. The solvent was removed in vacuo and the residue was partitioned between 10% aqueous sodium bicarbonate and 4:1 dichloromethane/isopropanol. The organic phase was dried (MgSO4) and concentrated to afford 1.24 g (66%) of N-[4-[[1-[2-(4-aminophenoxy)ethyl]-4-piperdinyl]carbonyl]phenyl]methanesulfonamide as a white foam which was used directly in the next step. 1H NMR (CDCl3): δ 7.85 (d, J=6 Hz, 2H), 7.23 (d, J=6 Hz, 2H), 6.63 (m, 4H), 4.21 (br s, 2H), 4.00 (m, 2H), 3.18 (m, 3H), 3.00 (s, 3H), 2.79 (m, 2H), 2.20 (m, 2H), 1.80 (m, 4H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between 10% aqueous sodium bicarbonate and 4:1 dichloromethane/isopropanol
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eb8d57efe97d4c8ab8f501db858641ca
Source dataset
uspto-grants-1993_10
Patent number
US05254689

Reaction notes

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