Nitrogen → HCID 10007429, compound

HRID 496035Notes

Reaction equation

HRID 496035 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:15](=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:11][CH2:10]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].N#N.CCOC(C)=O>C1COCC1>[F:34][C:31]1[CH:32]=[CH:33][C:28]([CH:20]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][N:12]2[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][O:6][C:5]3[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:14][CH2:13]2)=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 8857Ethyl AcetateHCID 10347573HCID 10347573, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10007429HCID 10007429, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{4-[2-(3,4-dimethoxy-phenoxy)ethyl]-piperazin-1-yl}-6,6-bis-(4-fluoro-phenyl)-hexan-1-one (0.7 g, 1.2 mmol) in THF (15 ml), was added LiAlH4 (100 mg, 2.4 mmol). The mixture was stirred at room temperature overnight (under N2). EtOAc was added and then washed with wate (2×10 ml), saturated NaCl (3×5 ml), dried over MgSO4, and evaporated under reduced pressure. The residue was purified by column chromatography on silica (CH2Cl2:MeOH 10:1) to give the desired product in 73% yield.

Workup

  1. washwashed with wate (2×10 ml), saturated NaCl (3×5 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica (CH2Cl2:MeOH 10:1)

Sources & evidence

ORD record
ord-b4cd2466bcae49d7aaf58750c9d895c1
Source dataset
uspto-grants-2005_09
Patent number
US06943168B2

Reaction notes

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