Hydrochloric Acid → 3-Fluoro-5-(1-methyl-piperidin-4-ylsulfanyl)-phenylamine

HRID 1822058Notes

Reaction equation

HRID 1822058 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:11][CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.Cl>[Fe].CO>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([S:11][CH:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]2)[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 578936894-(3-Fluoro-5-nitro-phenylsulfanyl)-1-methyl-piperidine

Product 1

HCID 578936763-Fluoro-5-(1-methyl-piperidin-4-ylsulfanyl)-phenylamineYield 40%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

Combine 4-(3-Fluoro-5-nitro-phenylsulfanyl)-1-methyl-piperidine (preparation 75, 0.31 g, 1.15 mmol), iron dust (0.21 g, 3.79 mmol), methanol (10 mL) and aqueous 1M hydrochloric acid (0.35 mL, 0.35 mmol), stir and heat at reflux. After 20 h, cool to ambient temperature and concentrate. Partition residue between ethyl acetate (50 mL) and 1M sodium hydroxide (20 mL). Separate the organic layer, dry over sodium sulfate, filter and concentrate. Purify residue by silica gel flash chromatography eluting with 10% (2M NH3/methanol)/methylene dichloride to obtain 0.11 g (40%) of the title compound: mass spectrum (electrospray): m/z=241.1 (M+1).

Workup

  1. temperatureheat
  2. temperatureat reflux
  3. concentrationconcentrate
  4. customSeparate the organic layer
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. washPurify residue by silica gel flash chromatography eluting with 10% (2M NH3/methanol)/methylene dichloride

Sources & evidence

ORD record
ord-62a6049ea3cf45ecac2a71f02f925584
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

Loading…