Hydrochloric Acid → HCID 59863034, compound

HRID 2064074Notes

Reaction equation

HRID 2064074 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([N+:23]([O-])=O)=[C:8]([NH:10][CH:11]3[CH2:16][CH2:15][N:14]([CH:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)[CH:9]=2)[CH2:3][CH2:2]1.[Sn](Cl)Cl.Cl>C(O)C>[CH:1]1([C:4]2[CH:9]=[C:8]([NH:10][CH:11]3[CH2:16][CH2:15][N:14]([CH:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)[C:7]([NH2:23])=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 59863025HCID 59863025, compound

Product 1

HCID 59863034HCID 59863034, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of N-(5-cyclopropyl-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D44, 150 mg, 0.43 mmol) and tin (II) chloride (326 mg, 1.72 mmol) in ethanol (10 ml) was treated with conc. HCl acid (˜0.38 ml) and heated at reflux temperature with stirring for 18 hrs. The solvent was removed by concentration under vacuum and the residue treated with dilute K2CO3 solution and extracted with ethyl acetate, filtering the mixture to remove tin residues. The separated organic phase was washed with water and brine, dried (MgSO4) and concentrated under vacuum to afford the title compound as a very pale brown sticky gum (114 mg, 83%). M++H=316.1.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature
  3. customThe solvent was removed by concentration under vacuum
  4. additionthe residue treated with dilute K2CO3 solution
  5. extractionextracted with ethyl acetate
  6. filtrationfiltering the mixture
  7. customto remove tin residues
  8. washThe separated organic phase was washed with water and brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-76743ce3401242918de8e98b6bcf722a
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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