Hydrochloric Acid → (R)-ethyl 4-(4-(amino(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoate hydrochloride salt

HRID 1771229Notes

Reaction equation

HRID 1771229 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C@H:15]([NH:33][S@](C(C)(C)C)=O)[CH:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[CH:5][CH:4]=1>CO>[ClH:2].[NH2:33][C@@H:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=1)[CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58080205ethyl 4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)benzoate2×

Product 1

HCID 86661881(R)-ethyl 4-(4-(amino(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoate hydrochloride saltYield 215%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HCl (1.16 ml, 4.63 mmol, 4.0 M in dioxane) was added to a solution of ethyl 4-(4-((R)-(4′-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)benzoate (INTERMEDIATE 128, 0.128 g, 0.23 mmol) in MeOH (3.5 ml) and the reaction mixture was stirred at r.t. for 3 hours. The reaction mixture was concentrated under reduced pressure and dried under vacuum to provide (R)-ethyl 4-(4-(amino(4′-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoate hydrochloride salt (INTERMEDIATE 133, STEP 1, 0.12 g), which was used in the preparation of INTERMEDIATE 133, STEP 2 without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customdried under vacuum

Sources & evidence

ORD record
ord-d3149f7e10ab4275ade66accf3cac13a
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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