Hydrochloric Acid → N,N-Dimethyl-1-(2-(methylamino)ethyl)-4-phenylpiperidin-4-amine tris hydrochloride

HRID 2387928Notes

Reaction equation

HRID 2387928 reaction equation
[ClH:1].[CH3:2][N:3]([CH3:27])[C:4]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12](C)[C:13](=O)OC(C)(C)C)[CH2:6][CH2:5]1.CO.C(Cl)(Cl)[Cl:31]>CCl>[ClH:31].[ClH:1].[ClH:31].[CH3:27][N:3]([CH3:2])[C:4]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][NH:12][CH3:13])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 21584188Chloroform methanol2×HCID 68408263tert-Butyl 2-(4-(dimethylamino)-4-phenylpiperidin-1-yl)ethyl(methyl)carbamate

Product 1

HCID 68409159N,N-Dimethyl-1-(2-(methylamino)ethyl)-4-phenylpiperidin-4-amine tris hydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 6327Methyl ChlorideSolvent

Procedure

HCl gas was passed for 30 minutes through a solution of 9 g (1 equiv.) of tert-butyl 2-(4-(dimethylamino)-4-phenylpiperidin-1-yl)ethyl(methyl)carbamate in 600 ml of CH3Cl. The progress of the reaction was monitored by means of thin-layer chromatography (20% MeOH/CHCl3). When the reaction was complete, HCl gas was passed through for a further 30 minutes and the complete reaction was again monitored by means of thin-layer chromatography (20% MeOH/CHCl3). When the reaction was complete, the solvent was removed under reduced pressure and 7.2 g (96%) of the desired product were obtained in the form of a white solid. The free base was obtained by dissolving the hydrochloride in aqueous sodium hydroxide solution and extracting with dichloromethane.

Workup

  1. customwas passed through for a further 30 minutes
  2. customthe complete reaction
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ce376efd522944e89171416f0d8c6a74
Source dataset
uspto-grants-2012_09
Patent number
US08269000B2

Reaction notes

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