trans N-benzyl-2-methoxy-N-[(2-methylcyclopropyl)methyl]ethanamine hydrochloride → trans (2-Methoxyethyl)[(2-methylcyclopropyl)methyl]amine hydrochloride

HRID 1944565Notes

Reaction equation

HRID 1944565 reaction equation
[ClH:1].C([N:9]([CH2:14][C@@H:15]1[CH2:17][C@H:16]1[CH3:18])[CH2:10][CH2:11][O:12][CH3:13])C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[ClH:1].[CH3:13][O:12][CH2:11][CH2:10][NH:9][CH2:14][C@@H:15]1[CH2:17][C@H:16]1[CH3:18]

Participants

4

Reactant 1

HCID 86616986trans N-benzyl-2-methoxy-N-[(2-methylcyclopropyl)methyl]ethanamine hydrochloride

Product 1

HCID 86616985trans (2-Methoxyethyl)[(2-methylcyclopropyl)methyl]amine hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of trans N-benzyl-2-methoxy-N-[(2-methylcyclopropyl)methyl]ethanamine hydrochloride (16 g, 59.3 mmol) in EtOH (400 mL), degassed with Argon, was added Pd(OH)2 (830 mg, 20%), and the mixture was stirred under 1 atm H2, at room temperature for 4 h. The reaction mixture was purged with N2, filtered on celite, under N2, concentrated in vacuo, and dried under vacuum over P2O5 to give trans (2-methoxyethyl)[(2-methylcyclopropyl)methyl]amine hydrochloride as a white foam. 1H NMR (400 MHz, CDCl3) δ 9.46 (bs, 2H), 3.84 (t, J=5.1 Hz, 2H), 3.40 (s, 3H), 3.23 (bt, J=5.1 Hz, 2H), 3.08-2.88 (m, 2H), 1.09 (d, J=6.1 Hz, 3H), 1.02-0.91 (m, 1H), 0.86-0.78 (m, 1H), 0.65-0.57 (m, 1H), 0.50-0.42 (m, 1H).

Workup

  1. customThe reaction mixture was purged with N2
  2. filtrationfiltered on celite, under N2
  3. concentrationconcentrated in vacuo
  4. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-1ad66e14bb2f4407b9f090686873b935
Source dataset
uspto-grants-2013_03
Patent number
US08394837B2

Reaction notes

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