Hydrochloric Acid → 1-[2-(Cyclopentyloxy)-3-methoxyphenyl]methanamine hydrochloride

HRID 453931Notes

Reaction equation

HRID 453931 reaction equation
[CH:1]1([O:6][C:7]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:8]=2[CH:9]=[N:10]O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H].[ClH:20]>CO.[Ni].C(OCC)(=O)C>[ClH:20].[CH:1]1([O:6][C:7]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:8]=2[CH2:9][NH2:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 86652761HCID 86652761, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 669167741-[2-(Cyclopentyloxy)-3-methoxyphenyl]methanamine hydrochloride

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of 2-(cyclopentyloxy)-3-methoxybenzaldehyde oxime (3 g, 12.448 mmol) in methanol (10 ml) was added catalytic amount of Raney nickel (0.30 g) at room temperature. The reaction mixture was stirred for 3 h at 50 psi hydrogen pressure in Paar hydrogenation apparatus. The reaction mixture was filtered through celite bed, dried (Na2SO4), filtered and concentrated to get the crude product. The crude product was then dissolved in ethyl acetate, to which hydrochloric acid in ethyl acetate was added dropwise at 10° C. and stirred for 20 min and then filtered and dried to yield 2.86 g of the product, 1H NMR (300 MHz, DMSO-d6) δ 1.57-1.63 (m, 4H), 1.65-1.72 (m, 4H), 3.81 (s, 3H), 3.94 (s, 2H), 4.90 (br s, 1H), 7.08 (s, 3H), 8.39 (br s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through celite bed
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto get the crude product
  6. additionwas added dropwise at 10° C.
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-02eb9c8cf03e4ff49a9491a2e67e7148
Source dataset
uspto-grants-2013_07
Patent number
US08492568B2

Reaction notes

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