tert-Butyl piperazine-1-carboxylate → HCID 69417178, compound

HRID 1295580Notes

Reaction equation

HRID 1295580 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[NH:8][C:7]=2[CH:13]=1)=O.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([CH2:1][C:3]2[CH:4]=[CH:5][C:6]3[O:11][CH2:10][C:9](=[O:12])[NH:8][C:7]=3[CH:13]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 107736383-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde

Product 1

HCID 69417178HCID 69417178, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 6-formyl-4H-benzo[1,4]oxazin-3-one (1.91 g, 10.8 mmol) and 1-(tert-butoxycarbonyl)piperazine (2.0 g, 10.8 mmol) in 1,2-dichloroethane (120 mL), was cooled in an ice-bath, and treated portionwise with sodium triacetoxyborohydride (3.43 g, 16.2 mmol) over 0.3 h, with stirring under argon. The resulting mixture was stirred at room temperature for 4 h, then partitioned between dichloromethane (100 mL) and saturated aqueous sodium bicarbonate. The organic layer was separated, dried (Na2SO4) and evaporated in vacuo to give the title compound (3.52 g, 94%) as a yellow oil.

Workup

  1. temperaturewas cooled in an ice-bath
  2. stirringThe resulting mixture was stirred at room temperature for 4 h
  3. custompartitioned between dichloromethane (100 mL) and saturated aqueous sodium bicarbonate
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ba0e2e6bbd744b10b7eb37a2f633ac3e
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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