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

HRID 229411Notes

Reaction equation

HRID 229411 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-da84500fe77d4d29952db6601728bbf2
Source dataset
uspto-grants-2009_07
Patent number
US07563806B2

Reaction notes

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