Sodium Hydroxide → 2-(2-Cyclopentyloxy-3-methoxy-phenyl)-ethylamine Hydrochloride

HRID 378970Notes

Reaction equation

HRID 378970 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([O:12][C:13]2[C:18]([CH:19]=[CH:20][N+:21]([O-])=O)=[CH:17][CH:16]=[CH:15][C:14]=2[O:24][CH3:25])[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Na+].[ClH:28].C(OCC)(=O)C>O1CCCC1.C(OCC)(=O)C.O>[ClH:28].[CH:7]1([O:12][C:13]2[C:14]([O:24][CH3:25])=[CH:15][CH:16]=[CH:17][C:18]=2[CH2:19][CH2:20][NH2:21])[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21866389Hydrogen chloride-ethyl acetateHCID 542993602-Cyclopentyloxy-1-methoxy-3-(2-nitro-vinyl)-benzene

Product 1

HCID 216972672-(2-Cyclopentyloxy-3-methoxy-phenyl)-ethylamine HydrochlorideYield 73%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A slurry under nitrogen of lithium aluminium hydride (3.5 g, 92.28 mmoles) in dry tetrahydrofuran (35 ml) was dropwise added under stirring with a solution of 2-cyclopentyloxy-1-methoxy-3-(2-nitro-vinyl)-benzene (8.1 g, 30.76 mmoles), obtained as described in example 2, in dry tetrahydrofuran (100 ml). At the end of the addition the mixture was refluxed for 2 hours more, then cooled in ice and slowly added with water (3.5 ml), 15% NaOH (3.5 ml) and water again (10.5 ml). Off the cooling bath, the stirring was kept on for another hour, then the solid was filtered off, and the solution was concentrated to small volume, diluted with ethyl acetate, washed with water, anhydrified over Na2SO4 and dried to give an oil which was dissolved in ethyl acetate (100 ml) and acidified with HCl/ethyl acetate. The product crystallized, thus was filtered and dried under vacuum at 40° C. to give 6.07 g of the title product (yield: 73%).

Workup

  1. customobtained
  2. additionAt the end of the addition the mixture
  3. temperaturewas refluxed for 2 hours more
  4. temperaturecooled in ice
  5. filtrationthe solid was filtered off
  6. concentrationthe solution was concentrated to small volume
  7. additiondiluted with ethyl acetate
  8. washwashed with water
  9. customdried
  10. customto give an oil which
  11. customThe product crystallized
  12. filtrationthus was filtered
  13. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-7bd45686ab604d8489e4d336fad9d15e
Source dataset
uspto-grants-2001_10
Patent number
US06297257B1

Reaction notes

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