Ethanol → HCID 3732956, compound

HRID 1699249Notes

Reaction equation

HRID 1699249 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1)(=[O:12])=[O:11])([O-])=O.C(O)C.O.O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH:14]1[CH2:15][CH2:16][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:18][CH2:19]1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 2435435HCID 2435435, compoundHCID 18321164HCID 18321164, compound

Product 1

HCID 3732956HCID 3732956, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 75.0 g (0.2 mol) of 2-nitro-N-[1-(phenylmethyl)-4-piperidinyl]-benzenesulphonic acid amide in 2.0 1 ethanol was added dropwise, at room temperature, a solution of 174.0 g (0.828 mol) of sodium dithionite-dihydrate in 700 ml of water. After the heat of the exothermic reaction had died away the mixture was refluxed for 4.5 hours, then the ethanol was distilled off and the aqueous phase remaining was extracted thoroughly with dichloromethane. The combined dichloromethane extracts were dried over sodium sulphate and evaporated down, the residue remaining was purified by column chromatography over silica gel using dichloromethane/methanol/conc. ammonia 80/20/0.25 (v/v/v) as eluant. 6.5 g (8.6% of theory) of a highly viscous oil were obtained.

Workup

  1. temperatureAfter the heat of the exothermic reaction
  2. temperaturewas refluxed for 4.5 hours
  3. distillationthe ethanol was distilled off
  4. extractionthe aqueous phase remaining was extracted thoroughly with dichloromethane
  5. dry with materialThe combined dichloromethane extracts were dried over sodium sulphate
  6. customevaporated down
  7. customthe residue remaining was purified by column chromatography over silica gel
  8. custom6.5 g (8.6% of theory) of a highly viscous oil were obtained

Sources & evidence

ORD record
ord-22686a39dfb1442db82bffc5323bec99
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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