Ethanol → HCID 67975039, compound

HRID 2174470Notes

Reaction equation

HRID 2174470 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8]C2CCNCC2)=[CH:4][C:3]=1[N+:17]([O-])=O.O.O.[Sn](Cl)Cl.[CH3:25][CH2:26]O>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][N:17]2[CH2:26][CH2:25][CH2:16][CH2:2][CH2:3]2)=[CH:4][C:3]=1[NH2:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 67974225HCID 67974225, compound

Product 1

HCID 67975039HCID 67975039, compoundYield 92%

Conditions

Temperature
60 °C

Procedure

4-(2-(4-chloro-3-nitrophenoxy)ethyl)piperidine (2.3 g, 8.1 mmol, 1 eq.) and tin (II) chloride dihydrate (9.1 g, 40.4 mmol, 5 eq.) were placed in EtOH (81 mL). The reaction mixture was heated at 60° C. and stirred for 19 hours. The reaction mixture was then concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic phase was washed with a 1N NaOH aqueous solution, dried over MgSO4, filtered and concentrated under reduced pressure to afford 2-chloro-5-(2-piperidinoethoxy)aniline (1.9 g, 92%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washThe organic phase was washed with a 1N NaOH aqueous solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f92da19c6a854a8eb69b3fe33935abac
Source dataset
uspto-grants-2015_06
Patent number
US09061999B2

Reaction notes

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