Hydrochloric Acid → HCID 14883414, compound

HRID 1461727Notes

Reaction equation

HRID 1461727 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:19]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[Sn].Cl>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:19]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5352426Tin atomHCID 14514742HCID 14514742, compound

Product 1

HCID 14883414HCID 14883414, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the mixture of N-(3-nitrophenyl)-N'-[3-(3-piperidinomethylphenoxy)propyl]urea (4.6 g) in ethanol (46 ml) was added tin (2.6 g). To the reaction mixture was added concentrated hydrochloric acid (1.9 ml) at room temperature under stirring, further added concentrated hydrochloric acid (18.2 ml) under heating on a water bath. The reaction mixture was refluxed for 6 hours, concentrated under reduced pressure, diluted with water (100 ml), alkalized with aqueous sodium hydroxide solution and extracted with dichloromethane (200 ml). The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the crude precipitate (3.8 g; yield 88.4%). This precipitate was recrystallized two times from ethanol to give the title compound (1.8 g), mp 116-118° C.

Workup

  1. temperatureunder heating on a water bath
  2. temperatureThe reaction mixture was refluxed for 6 hours
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with water (100 ml)
  5. extractionextracted with dichloromethane (200 ml)
  6. washThe organic layer was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give the crude precipitate (3.8 g; yield 88.4%)
  10. customThis precipitate was recrystallized two times from ethanol

Sources & evidence

ORD record
ord-8fb098e3f4004ab6a84e8220024a2188
Source dataset
uspto-grants-1991_12
Patent number
US05077302

Reaction notes

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