Hydrochloric Acid → HCID 59850164, compound

HRID 2064186Notes

Reaction equation

HRID 2064186 reaction equation
[CH:1]1([C:4]2[C:5]([F:26])=[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[CH2:12][CH2:13][N:14]([CH:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)[CH2:15][CH2:16]3)[C:7]([NH2:23])=[CH:6][C:5]=2[F:26])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 59850146HCID 59850146, compound

Product 1

HCID 59850164HCID 59850164, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of N-(5-cyclopropyl-4-fluoro-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D81, 0.38 g, 1.05 mmol), tin (II) chloride (0.8 mg, 4.20 mmol) and conc. HCl acid (˜0.9 ml) in abs ethanol (30 ml) was heated at gentle reflux temperature for 18 hrs. After cooling, the majority of solvent was removed by concentration under reduced pressure and the residue treated with dilute K2CO3 solution (50 ml) and extracted with ethyl acetate, filtering the mixture to remove tin residues. The separated organic phase was dried (MgSO4) and concentrated to dryness under vacuum to afford the title compound as a pale brown oil (340 mg, 97%).

Workup

  1. temperaturewas heated at gentle reflux temperature for 18 hrs
  2. temperatureAfter cooling
  3. customthe majority of solvent was removed by concentration under reduced pressure
  4. additionthe residue treated with dilute K2CO3 solution (50 ml)
  5. extractionextracted with ethyl acetate
  6. filtrationfiltering the mixture
  7. customto remove tin residues
  8. dry with materialThe separated organic phase was dried (MgSO4)
  9. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-ff3b20d8697e4a93aa63e8dd3dae8836
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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