Hydrogen chloride-ethyl acetate → 4-chloro-N-[(3R,4R)-3-(3,4-dichlorophenyl)-1-(piperidin-4-ylmethyl)piperidin-4-yl]-N-methylbenzamide Monohydrochloride

HRID 1260970Notes

Reaction equation

HRID 1260970 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]([CH3:39])[C@@H:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[CH2:13][C@H:12]2[C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=2)=[O:9])=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([C@@H:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:13][C@H:12]2[C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=2)[CH3:39])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68932507tert-butyl 4-{[(3R,4R)-4-{[(4-chlorophenyl)carbonyl](methyl)amino}-3-(3,4-dichlorophenyl)piperidin-1-yl]methyl}piperidine-1-carboxylate

Product 1

HCID 689301854-chloro-N-[(3R,4R)-3-(3,4-dichlorophenyl)-1-(piperidin-4-ylmethyl)piperidin-4-yl]-N-methylbenzamide MonohydrochlorideYield 168%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-{[(3R,4R)-4-{[(4-chlorophenyl)carbonyl] (methyl)amino}-3-(3,4-dichlorophenyl)piperidin-1-yl]methyl}piperidine-1-carboxylate (200 mg) obtained in Example 461 in ethyl acetate (4 mL) was added 4N hydrogen chloride/ethyl acetate (4 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure to give the title compound (150 mg, 85%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2636478c35ec494c97a4700ed18048ca
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

Loading…