Acetic Acid → HCID 43628950, compound

HRID 2403414Notes

Reaction equation

HRID 2403414 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[CH3:12][O:13][CH2:14][CH2:15][NH2:16].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH:16][CH2:15][CH2:14][O:13][CH3:12])[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 120720291-(Methylsulphonyl)piperidin-4-one

Product 1

HCID 43628950HCID 43628950, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methanesulphonyl-piperidine-4-one (182 mg; prepared from N—BOC-piperidone by reaction of piperidone-4-one TFA salt with methane sulphonyl chloride), stirring in anhydrous 1,2-dichloroethane (6 ml) was added 2-methoxyethylamine (90 μl) followed by glacial acetic acid (62 μl). Sodium triacetoxy borohydride (284 mg), was added in aliquots over 30 minutes and the reaction mixture stirred for 12 hours at room temperature, then diluted with dichloromethane (40 ml), washed with 50% NaHCO3 solution and dried (MgSO4). The solvents were removed in vacuo to give a residue which was purified by silica flash chromatography to give 1-methanesulphonyl-piperidin-4-yl-2-methoxy-ethylamine (148 mg), as a white solid.

Workup

  1. washwashed with 50% NaHCO3 solution
  2. dry with materialdried (MgSO4)
  3. customThe solvents were removed in vacuo
  4. customto give a residue which
  5. customwas purified by silica flash chromatography

Sources & evidence

ORD record
ord-66740ad65339499ba3e98c082a43dbf1
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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