Hydrochloric Acid → 1-(3,4-Dibromo-benzyl)-piperazine

HRID 40579Notes

Reaction equation

HRID 40579 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[C:17]([Br:22])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO.CCOCC>[Br:22][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[Br:21])[CH2:14][N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 578808894-(3,4-Dibromo-benzyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 32575461-(3,4-Dibromo-benzyl)-piperazineYield 108.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of 4-(3,4-dibromo-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (6.0 g) in MeOH (100 mL) was treated with 2 M HCl in Et2O (28 mL). After 16 h, the resulting suspension was diluted with Et2O (100 mL) and filtered. The solid was washed with Et2O (2×20 mL) and dried in vacuo, giving a white solid (5.0 g). This solid was partitioned between 10% aq. KOH (50 mL) and DCM (3×50 mL). The combined organic extracts were dried (MgSO4) and concentrated to give the title compound as a colorless glassy oil.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with Et2O (2×20 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-0649cd6f1e5d4b659d153ca6514b3430
Source dataset
uspto-grants-2013_09
Patent number
US08530476B2

Reaction notes

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