tert-Butyl piperazine-1-carboxylate → HCID 68626849, compound

HRID 1443033Notes

Reaction equation

HRID 1443033 reaction equation
C[C:2]1([CH:14]=O)[CH:7]=[CH:6][C:5](N2CCCCC2)=[CH:4][CH2:3]1.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[C-:29]#[N:30].C([Al+][CH2:34][CH3:35])C>ClCCCl.[Ti+4]>[C:29]([C:14]([CH:35]1[CH2:34][CH2:16][N:23]([CH3:28])[CH2:24][CH2:25]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[N:26]1[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28][CH2:27]1)#[N:30]

Participants

6

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 16686413Diethyl aluminum cyanideHCID 86622687HCID 86622687, compound

Product 1

HCID 68626849HCID 68626849, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 114942Titanium cation (4+)CatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1-methyl-4-piperidinyl phenyl methanone 1.218 g (6 mmol), N-Boc piperazine 1.118 g (6 mmol) and titanium (IV) isoproxide 1.77 ml (6 mmol) in 1,2-dichloroethane (25 ml) was stirred at room temperature for 72 hours. Diethylaluminum cyanide (1M solution in toluene) 12 ml was added and the reaction mixture was stirred for another 24 hours. The reaction was quenched with saturated sodium bicarbonate solution (20 ml) and filtered. The filtrate was extracted with ethyl acetate twice. The combined ethyl acetate solution was washed with more saturated sodium bicarbonate solution and brine, dried over sodium sulfate, concentrated and applied to flash column chromatography using methylene chloride and methanol (100:2.5) as eluent to give 0.6 g of desired product in 25% yield.

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate solution (20 ml)
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with ethyl acetate twice
  4. washThe combined ethyl acetate solution was washed with more saturated sodium bicarbonate solution and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3264da625a884833bc7e4efcf15e06be
Source dataset
uspto-grants-2010_02
Patent number
US07659395B2

Reaction notes

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