Sodium Bicarbonate → HCID 69144950, compound

HRID 2223937Notes

Reaction equation

HRID 2223937 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([NH:7]C2CCNCC2)=[CH:3][CH:2]=1.[CH2:15]([N:22]1[CH2:27][CH2:26][C:25]([CH2:48][CH:49]=O)([CH2:28][CH2:29][O:30][Si:31]([C:44]([CH3:47])([CH3:46])[CH3:45])([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O[BH-](O[C:61](=O)[CH3:62])OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(N(CC)CC)C>[CH2:15]([N:22]1[CH2:23][CH2:24][C:25]([CH2:48][CH2:49][C:1]2([CH3:14])[CH:2]=[CH:3][C:4]([NH:7][N:7]3[CH2:62][CH2:61][CH2:2][CH2:3][CH2:4]3)=[CH:5][CH2:6]2)([CH2:28][CH2:29][O:30][Si:31]([C:44]([CH3:47])([CH3:46])[CH3:45])([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:26][CH2:27]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23020914N-(4-Methylphenyl)-4-piperidinamineHCID 59714908HCID 59714908, compound

Product 1

HCID 69144950HCID 69144950, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a suspension of 4-(p-toluidino)piperidine ditrifluoroacetate (synthesized in Preparation Example 4-5) (0.63 g) in 1,2-dichloroethane (3 mL) was added triethylamine (0.42 mL). The suspension was stirred at room temperature for 25 minutes. Then, to the suspension was added [1-benzyl-4-[2-(tert-butyldiphenylsiloxy)ethyl]piperidin-4-yl]acetaldehyde (synthesized in Example 85) (0.75 g) in 1,2-dichloroethane (1.5 mL), and it was stirred at room temperature for additional 5 minutes. The reaction solution was ice-cooled, to which sodium triacetoxyborohydride (0.50 g) was added. After allowing the temperature to rise to room temperature, the solution was stirred for additional 15 hours. Saturated aqueous sodium bicarbonate solution was and it was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [NH silica gel, ethyl acetate-chloroform (5:95)] to give the title compound (0.87 g).

Workup

  1. stirringwas stirred at room temperature for additional 5 minutes
  2. additionwas added
  3. customto rise to room temperature
  4. stirringthe solution was stirred for additional 15 hours
  5. extractionit was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by chromatography [NH silica gel, ethyl acetate-chloroform (5:95)]

Sources & evidence

ORD record
ord-7359c76209a64d9283ec95006fd4b7ca
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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