1-Acetylpiperazine → HCID 69021862, compound

HRID 1864764Notes

Reaction equation

HRID 1864764 reaction equation
[C:1]([N:4]1[C@:8]([CH2:15][CH2:16][CH:17]=O)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][C:6]([C:19]2[CH:24]=[C:23]([Br:25])[CH:22]=[CH:21][C:20]=2[F:26])=[N:5]1)(=[O:3])[CH3:2].[C:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])[CH3:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:27]([N:30]1[CH2:35][CH2:34][N:33]([CH2:17][CH2:16][CH2:15][C@:8]2([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:4]([C:1](=[O:3])[CH3:2])[N:5]=[C:6]([C:19]3[CH:24]=[C:23]([Br:25])[CH:22]=[CH:21][C:20]=3[F:26])[CH2:7]2)[CH2:32][CH2:31]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 837951-AcetylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86622382HCID 86622382, compound

Product 1

HCID 69021862HCID 69021862, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 57 mg (0.137 mmol) 3-6 in 1.0 mL of anhydrous DCE under Ar was added 26.3 mg (0.206 mmol) 1-acetylpiperazine followed by 58.1 mg (0.274 mmol) sodium triacetoxyborohydride. The mixture stirred overnight before quenching with saturated aqueous NaHCO3 solution and adding a small amount of DCM. The aqueous phase was re-extracted with DCM and the organic phases were loaded directly onto silica gel for flash chromatography using a mixture of hexanes, EtOAc, and 20:1:1 EtOH—NH4OH—H2O to give 3-7 as a white solid.

Workup

  1. custombefore quenching with saturated aqueous NaHCO3 solution
  2. additionadding a small amount of DCM
  3. extractionThe aqueous phase was re-extracted with DCM
  4. additiona mixture of hexanes, EtOAc, and 20:1:1 EtOH—NH4OH—H2O

Sources & evidence

ORD record
ord-eda68ef2a811446e9f1aa357ac8f01a8
Source dataset
uspto-grants-2009_12
Patent number
US07625936B2

Reaction notes

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