Sodium triacetoxyborohydride → 4-[(4-tert-Butylmorpholin-2-yl)methyl]-N-(3,4-dichlorophenyl)piperazine-1-carboxamide

HRID 603256Notes

Reaction equation

HRID 603256 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][O:8][CH:7]([CH:11]=O)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[O:23])[CH:17]=[CH:18][C:19]=1[Cl:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:1]([N:5]1[CH2:10][CH2:9][O:8][CH:7]([CH2:11][N:27]2[CH2:26][CH2:25][N:24]([C:22]([NH:21][C:16]3[CH:17]=[CH:18][C:19]([Cl:20])=[C:14]([Cl:13])[CH:15]=3)=[O:23])[CH2:29][CH2:28]2)[CH2:6]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 16775732N-(3,4-Dichlorophenyl)piperazine-1-carboxamideHCID 576569134-Tert-butylmorpholine-2-carbaldehyde

Product 1

HCID 576567394-[(4-tert-Butylmorpholin-2-yl)methyl]-N-(3,4-dichlorophenyl)piperazine-1-carboxamideYield 19.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-tert-butylmorpholine-2-carbaldehyde (154 mg) and N-(3,4-dichlorophenyl)piperazine-1-carboxamide (247 mg) in dichloromethane (20 mL) was stirred at room temperature under argon. Sodium triacetoxyborohydride (381 mg) was added and the mixture was stirred overnight. The reaction was quenched with water and partitioned between water and dichloromethane. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and then brine, dried (Na2SO4), filtered and concentrated. The residue was purified on the Isco™ Companion (12 g column: 0-11% MeOH in DCM) to give the title compound as a white solid (75 mg).

Workup

  1. customThe reaction was quenched with water
  2. custompartitioned between water and dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialbrine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on the Isco™ Companion (12 g column: 0-11% MeOH in DCM)

Sources & evidence

ORD record
ord-8797c8f9f8764bd697c5284f6f3bada2
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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