Water → Racemic benzyl 3-(hydroxymethyl)-3-methylpiperazine-1-carboxylate

HRID 502527Notes

Reaction equation

HRID 502527 reaction equation
[CH3:1][C:2]1([CH2:8][OH:9])[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[C:10](ON1C(=O)CCC1=O)([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].O.[OH-].[Na+]>CC#N.CC(N(C)C)=O.O.CC(N(C)C)=O.[Cl-].[Na+].O>[OH:9][CH2:8][C:2]1([CH3:1])[NH:3][CH2:4][CH2:5][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:7]1

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 83172Benzyl succinimido carbonateHCID 55300708(2-Methylpiperazin-2-yl)methanol

Product 1

HCID 68459606Racemic benzyl 3-(hydroxymethyl)-3-methylpiperazine-1-carboxylateYield 96.6%

Reagents, catalysts & solvents 3

HCID 31374DimethylacetamideSolventHCID 57417360Sodium chloride; waterSolventHCID 87231873CH3CN Dma H2OSolvent

Conditions

Temperature
0 °C

Procedure

To crude (2-methylpiperazin-2-yl)methanol (10 C) (0.042 mol) dissolved in CH3CN/DMA/H2O (20 mL, 20 mL, 20 mL) cooled to 0° C. was added CBZ-OSu (9.5 g, 0.038 mol) in DMA (15 mL). The reaction was stirred at 0° C. for 30 min then warmed to RT. To the mixture was added H2O (500 mL), sat'd brine (50 mL) and 1M NaOH (50 mL), then the residue was extracted four times with EtOAc (100 mL). The combined EtOAc layers were washed twice with brine then dried over MgSO4 and the solvent removed in vacuo to give racemic benzyl 3-(hydroxymethyl)-3-methylpiperazine-1-carboxylate (9.7 g). HPLC RT: 1.302 min (4 min Chromolith column TFA).

Workup

  1. temperaturethen warmed to RT
  2. extractionthe residue was extracted four times with EtOAc (100 mL)
  3. washThe combined EtOAc layers were washed twice with brine
  4. dry with materialthen dried over MgSO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4617f6dab971444d813b29d38cf940c0
Source dataset
uspto-grants-2010_08
Patent number
US07776859B2

Reaction notes

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