Hydrochloric Acid → (S)-2-Benzylpiperazine

HRID 1972428Notes

Reaction equation

HRID 1972428 reaction equation
Cl.[CH2:2]([C@@H:9]1[NH:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(Cl)Cl>[CH2:2]([C@H:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24820349tert-Butyl (3S)-3-benzylpiperazine-1-carboxylate

Product 1

HCID 20760001(S)-2-BenzylpiperazineYield 141.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl (4.0 M solution with 1,4-dioxane, 45 mL, 180 mmol) was added to a stirring solution of tert-butyl (3S)-3-benzyl-1-piperazinecarboxylate (5.0 g, 18 mmol, Waterstone Technology, Carmel, Ind.) and CH2Cl2 (36 mL) at room temperature. After 16 h, the reaction mixture was concentrated to give 4.5 g (2S)-2-benzylpiperazine (4.5 g) as its dihydrochloride salt. The material was used in the next step without purification.

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-c0cbf5431e9f4b79bb179d966e8ccb3e
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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