tert-Butyl piperazine-1-carboxylate → HCID 57897266, compound

HRID 416789Notes

Reaction equation

HRID 416789 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[O:10][N:9]=[C:8]([CH3:11])[CH:7]=1)=[O:4].[C:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>ClCCl>[CH3:11][C:8]1[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:22]2[CH2:21][CH2:20][N:19]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:24][CH2:23]2)[O:10][N:9]=1

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 133629642-Bromo-N-(3-methylisoxazol-5-yl)acetamide

Product 1

HCID 57897266HCID 57897266, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-bromo-N-(3-methylisoxazol-5-yl)acetamide (0.122 g, 0.58 mmol) in anhydrous dichoromethane (4.5 ml) under argon was added 1-BOC-piperazine (0.241 g, 1.30 mmol). The reaction mixture was stirred at room temperature for 2 h under argon, then partitioned between ethyl acetate (100 ml) and 6% aqueous Na2CO3 (50 ml). The organic layer was washed with more 6% aqueous Na2CO3 (50 ml), and concentrated in vacuo. The residue was absorbed on silica gel and the free-running powder was placed on a 10 g isolute column. Elution of the column with 30% ethyl acetate in dichloromethane afforded the title compound as a white solid (0.096 g, 51%). 1H-NMR (500 MHz, DMSO-d6) 1.39 (s, 9H, C(CH3)3), 2.18 (s, 3H, CH3), 2.45 (t, J=5.1 Hz, 4H, piperazine N(CH2)2), 3.23 (s, 2H, NCH2CO), 3.34 (t, J=4.7 Hz, 4H, piperazine N(CH2)2), 6.13 (s, 1H, isoxazole C—H), 11.28 (s, 1H, CONH);

Workup

  1. custompartitioned between ethyl acetate (100 ml) and 6% aqueous Na2CO3 (50 ml)
  2. washThe organic layer was washed with more 6% aqueous Na2CO3 (50 ml)
  3. concentrationconcentrated in vacuo
  4. customThe residue was absorbed on silica gel
  5. washElution of the column with 30% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-157ff2db46c049258b42eca970600324
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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