Hydrochloric Acid → 4-chloro-N1-(tetrahydro-pyran-4-ylmethyl)-benzene-1,2-diamine

HRID 469723Notes

Reaction equation

HRID 469723 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[C:4]([N+:16]([O-])=O)[CH:3]=1.[Sn].Cl.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([NH:8][CH2:9][CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 62349965(4-Chloro-2-nitro-phenyl)-(tetrahydro-pyran-4-ylmethyl)-amine

Product 1

HCID 637259554-chloro-N1-(tetrahydro-pyran-4-ylmethyl)-benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-chloro-2-nitro-phenyl)-(tetrahydro-pyran-4-ylmethyl)-amine (1.28 g; 4.729 mmol) in tetrahydrofuran (25 mL) was added tin metal (1.740 g; 14.660 mmol) and 1N hydrochloric acid (32.157 mL; 32.157 mmol) and the reaction is stirred at room temperature overnight. After this time, the mixture is diluted with 1N sodium hydroxide solution (1.6 g NaOH/40 mL water; 40 mmol) and filtered through Celite®, washing with ethyl acetate. The filtrate is extracted with ethyl acetate and the combined organics are washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford title compound which was used without further purification. ESI m/z 241 [M+H]+

Workup

  1. filtrationfiltered through Celite®
  2. washwashing with ethyl acetate
  3. extractionThe filtrate is extracted with ethyl acetate
  4. washthe combined organics are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23bacb4b87f04c2bbb88e98ec79c030c
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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