Sodium Bicarbonate → 2-[1-[2-[4-(p-Toluidino)piperidin-1-yl]ethyl]cyclooctyl]ethanol

HRID 2223931Notes

Reaction equation

HRID 2223931 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([NH:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:3][CH:2]=1.[CH2:15]1[C:20]2([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:19][CH2:18][O:17][CH:16]1O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(N(CC)CC)C>[C:1]1([CH3:14])[CH:2]=[CH:3][C:4]([NH:7][CH:8]2[CH2:13][CH2:12][N:11]([CH2:18][CH2:19][C:20]3([CH2:15][CH2:16][OH:17])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:10][CH2:9]2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23020914N-(4-Methylphenyl)-4-piperidinamineHCID 597149153-Oxaspiro[5.7]tridecan-2-ol

Product 1

HCID 597148642-[1-[2-[4-(p-Toluidino)piperidin-1-yl]ethyl]cyclooctyl]ethanolYield 45.5%

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) (1.31 g) in 1,2-dichloroethane (6 mL) was added triethylamine (0.96 mL). The suspension was stirred at room temperature for 5 minutes. Then, a solution of 3-oxaspiro[5.7]tridecan-2-ol (synthesized in Example 72) (0.62 g) in 1,2-dichloroethane (3 mL) was added to the suspension, and it was stirred at room temperature for additional 10 minutes. The reaction solution was ice-cooled and sodium triacetoxyborohydride (0.70 g) was added thereto. The reaction solution was then allowed for its temperature to rise to room temperature, and the solution was stirred for additional 4.5 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction solution and it was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, methanol-chloroform (3:97 to 1:9)] to give the title compound (0.53 g).

Workup

  1. stirringwas stirred at room temperature for additional 10 minutes
  2. temperaturecooled
  3. customto rise to room temperature
  4. stirringthe solution was stirred for additional 4.5 hours
  5. extractionwas extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by chromatography [silica gel, methanol-chloroform (3:97 to 1:9)]

Sources & evidence

ORD record
ord-a33a41345cae424fa0c7a6b8c2d0cf29
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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