Acetic Acid → N-(2-methoxyethyl)-1-methylpiperidin-4-amine

HRID 2403416Notes

Reaction equation

HRID 2403416 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[CH3:9][O:10][CH2:11][CH2:12][NH2:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH3:9][O:10][CH2:11][CH2:12][NH:13][CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 13603N-Methyl-2-piperidoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 2761027N-(2-methoxyethyl)-1-methylpiperidin-4-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-methyl-piperidone (1.00 g) in 1,2-dichloroethane (20 ml) was added 2-methoxyethylamine (0.77 ml), followed by sodium triacetoxyborohydride (2.62 g) and acetic acid (0.53 g). The reaction mixture was stirred at room temperature overnight. Dichloromethane/aqueous sodium hydrogen carbonate extraction and purification on silica gave (2-methoxy-ethyl)-(1-methyl-piperidin-4-yl)-amine (1.52 g).

Workup

  1. extractionDichloromethane/aqueous sodium hydrogen carbonate extraction and purification on silica

Sources & evidence

ORD record
ord-d86007f829d74984a902edeb0cf19eec
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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