Hydrogen Bromide → (3S,5R)-1-(4-chloro-quinolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one

HRID 1432911Notes

Reaction equation

HRID 1432911 reaction equation
Br.C(OC([N:12]1[C@H:17]([CH3:18])[CH2:16][N:15]([CH2:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24]([Cl:30])=[CH:25][CH:26]=[N:27]3)=[CH:22][CH:21]=2)[C:14](=[O:31])[C@@H:13]1[CH3:32])=O)C1C=CC=CC=1.C(N(CC)CC)C>C(O)(=O)C.C(OCC)(=O)C>[Cl:30][C:24]1[C:23]2[C:28](=[CH:29][C:20]([CH2:19][N:15]3[CH2:16][C@@H:17]([CH3:18])[NH:12][C@@H:13]([CH3:32])[C:14]3=[O:31])=[CH:21][CH:22]=2)[N:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 8471TriethylamineHCID 57020279(2S,6R)-4-(4-chloro-quinolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 57264969(3S,5R)-1-(4-chloro-quinolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-oneYield 81%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 33% solution of hydrogen bromide in acetic acid (10 mL) is added to (2S,6R)-4-(4-chloro-quinolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (1.04 g, 2.38 mmol). The reaction is left to stir at room temperature for one hour. The reaction mixture is diluted with ethyl acetate and stirred vigorously to force the product to precipitate out of solution. The ethyl acetate is decanted off and the precipitate is purified on a silica gel column (1% triethylamine/3% methanol/methylene chloride) to 582 mg (81% yield) of (3S,5R)-1-(4-chloro-quinolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one as a white solid.

Workup

  1. waitThe reaction is left
  2. stirringstirred vigorously
  3. customto precipitate out of solution
  4. customThe ethyl acetate is decanted off

Sources & evidence

ORD record
ord-0c16b595a96c408da4a3b628243ad179
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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