HCID 19004204, compound → HCID 19004206, compound

HRID 2225432Notes

Reaction equation

HRID 2225432 reaction equation
[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][CH2:16][N:13]2[CH2:12][CH2:11][CH:10]([CH2:9][O:8][CH:7]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:15][CH2:14]2)=[CH:23][CH:22]=1

Participants

3

Reactant 1

HCID 19004204HCID 19004204, compound

Product 1

HCID 19004206HCID 19004206, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-(diphenylmethoxymethyl)-1-(4-nitrophenethyl)piperidine (1.40 g, 3.3 mmol) (see Example 13) and stannous (II) dichloride dihydrate (3.68 g, 16.3 mmol) in ethanol (20 ml) was heated at 70° C. for 2 hours, allowed to cool to room temperature and filtered. The filtrate was evaporated and the residue partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution. The layers were separated and the aqueous layer extracted into ethyl acetate. The combined organic layers were washed with saturated brine, dried over magnesium sulphate and evaporated. The residue was triturated with ether and the resulting solid collected, washed with ether and dried to give the title compound (0.66 g) as a fawn solid, m.p. 188°-190° C., which was characterized by its 1H-NMR spectrum.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted into ethyl acetate
  7. washThe combined organic layers were washed with saturated brine
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customThe residue was triturated with ether
  11. customthe resulting solid collected
  12. washwashed with ether
  13. customdried

Sources & evidence

ORD record
ord-04d0ec52e84c423d96db529c334b0ca9
Source dataset
uspto-grants-1994_09
Patent number
US05344835

Reaction notes

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