Hydrochloric Acid → 1-(4-Methoxy-benzyl)-cyclopentylamine

HRID 229411ノート

反応式

HRID 229411 の反応式
Cl.[NH2:2][C:3]1([CH2:8][C:9]2[CH:14]=[CH:13][C:12](N)=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.Cl.N([O-])=O.[Na+].[CH3:21][OH:22]>O>[CH3:21][O:22][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:3]2([NH2:2])[CH2:7][CH2:6][CH2:5][CH2:4]2)=[CH:10][CH:11]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 231061154-(1-Aminocyclopentylmethyl)-phenylamine hydrochlorideHCID 23668193Sodium Nitrite

生成物 1

HCID 231060841-(4-Methoxy-benzyl)-cyclopentylamine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

1.4 g (6.17 mmol) 4-(1-aminocyclopentylmethyl)-phenylamine hydrochloride are placed in 25 mL methanol and at 0° C. combined with 2.24 mL (27 mmol) conc. hydrochloric acid. At this temperature 0.51 g (7.41 mmol) sodium nitrite in 1 mL water are added dropwise within 30 minutes. After 2 hours stirring the reaction mixture is allowed to come up to ambient temperature and then refluxed for 3 hours. The solvents are distilled off and the residue is combined with ethyl acetate. It is washed with aqueous ammonia solution, dried with sodium sulphate and evaporated down. The residue is dissolved in ethanol and combined with 10% hydrochloric acid in ethanol. The product precipitated as a salt is filtered off, washed with ethanol and dried. Yield: 0.56 g (27% over 2 steps, hydrochloride), mass spectroscopy: [M+H]+=206.

後処理

  1. customto come up to ambient temperature
  2. temperaturerefluxed for 3 hours
  3. distillationThe solvents are distilled off
  4. washIt is washed with aqueous ammonia solution
  5. dry with materialdried with sodium sulphate
  6. customevaporated down
  7. dissolutionThe residue is dissolved in ethanol
  8. customThe product precipitated as a salt
  9. filtrationis filtered off
  10. washwashed with ethanol
  11. customdried

出典と根拠

ORDレコード
ord-da84500fe77d4d29952db6601728bbf2
出典データセット
uspto-grants-2009_07
特許番号
US07563806B2

反応ノート

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