Hydrochloric Acid → N,N-Dimethyl-1-(3-(methylamino)propyl)-4-phenylpiperidin-4-amine hydrochloride

HRID 453897Notes

Reaction equation

HRID 453897 reaction equation
Cl.[CH3:2][N:3]([CH3:28])[C:4]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][N:13](C)[C:14](=O)OC(C)(C)C)[CH2:6][CH2:5]1.CO.C(Cl)(Cl)[Cl:32]>C(Cl)(Cl)Cl>[ClH:32].[CH3:28][N:3]([CH3:2])[C:4]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][NH:13][CH3:14])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21584188Chloroform methanolHCID 68494485Tert-butyl 3-(4-(dimethylamino)-4-phenylpiperidin-1-yl)propyl(methyl)carbamate

Product 1

HCID 68496686N,N-Dimethyl-1-(3-(methylamino)propyl)-4-phenylpiperidin-4-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

HCl gas was passed through a solution of 9 g (1 eq.) tert-butyl 3-(4-(dimethylamino)-4-phenylpiperidin-1-yl)propyl(methyl)carbamate in 100 ml chloroform at 0° C. for 1 h. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). Once the conversion was complete, the solvent was removed under reduced pressure and after trituration with diethyl ether 10 g (100%) of product were obtained in the form of a white solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customafter trituration with diethyl ether 10 g (100%) of product were obtained in the form of a white solid

Sources & evidence

ORD record
ord-495926fbcbb74c62915604fda4a31484
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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