tert-Butyl piperazine-1-carboxylate → HCID 46867019, compound

HRID 416804Notes

Reaction equation

HRID 416804 reaction equation
Br[CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1.[C:9]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>ClCCl>[C:12]([O:11][C:9]([N:16]1[CH2:21][CH2:20][N:19]([CH2:2][C:3]2[CH:7]=[C:6]([CH3:8])[O:5][N:4]=2)[CH2:18][CH2:17]1)=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27763043-(Bromomethyl)-5-methylisoxazole

Product 1

HCID 46867019HCID 46867019, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromomethyl-5-methylisoxazole (0.102 g, 0.58 mmol) in dichloromethane (6 ml) was added 1-BOC-piperazine (0.240 g, 1.30 mmol). The reaction mixture was stirred at room temperature for 18 h under argon, then concentrated in vacuo. The resulting residue was absorbed on silica and the free-running powder was placed on a 10 g isolute silica column. Elution with a gradient of ethyl acetate (30 to 70%) in petroleum ether (60-80° C.) afforded the title compound as a white solid (0.124 g, 76%). 1H-NMR (500 MHz, DMSO-d6) 1.39 (s, 9H, C(CH3)3), 2.32 (t, J=5.1 Hz, 4H, piperazine N(CH2)2), 2.38 (s, 3H, isoxazole 5-CH3), 3.35 (br t, 4H, piperazine N(CH2)2), 3.50 (s, 2H, NCH2 isoxazole), 6.17 (s, 1H, isoxazole 4-H); LC (Method B)-MS (ESI, m/z): Rt=2.60 min—282 [(M+H)+, 5%], 226 [(M-tBu)+, 100%].

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was absorbed on silica
  3. washElution with a gradient of ethyl acetate (30 to 70%) in petroleum ether (60-80° C.)

Sources & evidence

ORD record
ord-95a36a3184da4c72bf7a00b5f62cbc46
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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