Acetic Acid → HCID 10330528, compound

HRID 1260256Notes

Reaction equation

HRID 1260256 reaction equation
[C:1]1([C@@H:7]2[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[CH:17](=O)[CH2:18][CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[C:1]1([C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([CH2:17][CH2:18][CH3:19])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 101021(S)-3-PhenylpiperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10330528HCID 10330528, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1 g (6.2 mmol) of commercially available (S)-3-phenylpiperidine was dissolved in dichloromethane and 0.37 ml acetic acid (6.51 mmol). After addition of 0.5 ml of propanal (6.93 mmol) and 1.97 g of sodium triacetoxyborohydride (9.3 mmol), the reaction mixture was stirred at room temperature for 18 h. Water was added, the layers separated, and the aqueous phase extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and evaporated to dryness to yield 1.1 g of (S)-3-phenyl-1-propyl-piperidine.

Workup

  1. customthe layers separated
  2. extractionthe aqueous phase extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-b286245aa1284d768b3cb4174f0f8713
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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