Water → benzyl (3S)-4-(bromoacetyl)-3-(hydroxymethyl)piperazine-1-carboxylate

HRID 2063315Notes

Reaction equation

HRID 2063315 reaction equation
Cl.[OH:2][CH2:3][C@H:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1.CCN(C(C)C)C(C)C.[Br:29][CH2:30][C:31](Cl)=[O:32].O>C(Cl)Cl>[Br:29][CH2:30][C:31]([N:9]1[CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5][C@H:4]1[CH2:3][OH:2])=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chlorideHCID 16124474(S)-benzyl 3-(hydroxymethyl)piperazine-1-carboxylate hydrochloride

Product 1

HCID 16124473benzyl (3S)-4-(bromoacetyl)-3-(hydroxymethyl)piperazine-1-carboxylateYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate hydrochloride (0.83 g, 2.9 mmol) was dissolved in methylene chloride (10 mL) together with DIPEA (1.5 mL, 8.6 mmol). Bromoacetyl chloride (0.48 g, 3.0 mmol) was added at 0° C. by means of drops. The mixture was stirred at RT for 1 h and then water (10 mL) was added. The phases were separated by means of a phase separator column. The organic solution was collected and the solvent was removed by evaporation. There was obtained 1.1 g (100%) of benzyl (3S)-4-(bromoacetyl)-3-(hydroxymethyl)piperazine-1-carboxylate as a brown oil. LCMS: m/z 370 (M−1)−.

Workup

  1. customThe phases were separated by means of a phase separator column
  2. customThe organic solution was collected
  3. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-f9069837fb024b9d97218fe12b004a5d
Source dataset
uspto-grants-2012_10
Patent number
US08288370B2

Reaction notes

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