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

HRID 1822058ノート

反応式

HRID 1822058 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-62a6049ea3cf45ecac2a71f02f925584
出典データセット
uspto-grants-2009_10
特許番号
US07608629B2

反応ノート

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