Acetic Acid → 3-(1-Methylpiperidin-4-yl)propan-1-ol

HRID 1986167Notes

Reaction equation

HRID 1986167 reaction equation
C=O.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][OH:12])[CH2:5][CH2:4]1.[C:13]([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C>[CH3:13][N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][OH:12])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 814974-PiperidinepropanolHCID 5003444Sodium cyanoborohydride

Product 1

HCID 155406773-(1-Methylpiperidin-4-yl)propan-1-olYield 81.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Formalin (6.33 g, 211 mmol) is added to a stirred solution of 3-(piperidin-4-yl)-propan-1-ol (3.02 g, 21.1 mmol) in acetonitrile (30 mL) at ambient temperature. The solution is allowed to stir for 20 minutes. Sodium cyanoborohydride (3.31 g, 52.7 mmol) and acetic acid (3 mL) are sequentially added to the reaction mixture and the resultant mixture is stirred for another 2 hours. After concentration, the crude product is dissolved in dichloromethane (150 mL), washed with saturated aqueous NaHCO3 (60 mL×2), dried and concentrated. The crude product is subjected to chromatography on silica gel and eluted with 2 M NH3/CH3OH in dichloromethane 0-15% to give the title compound as an oil (2.70 g).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe crude product is dissolved in dichloromethane (150 mL)
  3. washwashed with saturated aqueous NaHCO3 (60 mL×2)
  4. customdried
  5. concentrationconcentrated
  6. washeluted with 2 M NH3/CH3OH in dichloromethane 0-15%

Sources & evidence

ORD record
ord-5b449970ce074d9fb80ce153d48444e5
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

Loading…