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

HRID 1500317Notes

Reaction equation

HRID 1500317 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 hydrochloride

Reagents, catalysts & solvents 1

HCID 6327Methyl ChlorideSolvent

Procedure

HCl gas was passed through a solution of 9 g (1 eq) tert-butyl 2-(4-(dimethylamino)-4-phenylpiperidin-1-yl)ethyl(methyl)carbamate in 600 ml CH3Cl for 30 min. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). Once the conversion was complete, the passage of HCl gas was continued for a further 30 min and the completeness of the conversion again monitored by thin-layer chromatography (20% MeOH/CHCl3). Once the conversion was complete, the solvent was removed under reduced pressure and 7.2 g (96%) of the desired product obtained in the form of a white solid.

Workup

  1. customthe solvent was removed under reduced pressure and 7.2 g (96%) of the desired product
  2. customobtained in the form of a white solid

Sources & evidence

ORD record
ord-8e6949b7860346998014d637d1e1443a
Source dataset
uspto-grants-2015_12
Patent number
US09206156B2

Reaction notes

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