HCID 12972966, compound → HCID 12972966, compound

HRID 324555Notes

Reaction equation

HRID 324555 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([OH:18])[CH2:16][OH:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Br>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH:14]2[CH2:15][O:18][C:15]([CH3:16])([CH3:14])[O:18]2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH:15]([OH:18])[CH2:16][OH:17])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 12972966HCID 12972966, compound

Product 2

HCID 12972966HCID 12972966, compoundYield 80%HCID 18621460HCID 18621460, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
25 °C

Procedure

4-Benzyl-1-(2,3-dihydroxypropyl)piperidine. A solution of 4-(4-Benzyl-piperidin-1-yl)-2,2-dimethyl-1,3-dioxolane (0.65 g) in methanolic HBr (1.0 M, 20 mL) was prepared. The solution was stirred at 25° C. for 2 h then was concentrated in vacuo. The resulting crude product was dissolved in water (50 mL), washed with ether (20 mL), made basic with saturated NaHCO3 (20 mL) and extracted with CH2Cl2 (3×30 mL). The crude compound was purified by trituration with EtOAc (5 mL) for 2 h to give the title compound as a colorless solid (0.45 g, 80%): mp 92-94oC; 1H NMR (CDCl3) δ 1.15-1.40 (m, 2H), 1.45-1.65 (m, 1H), 1.64 (bd, J=13.5 Hz, 2H), 1.92 (t, J=11.4 Hz, 1H), 2.20 (t, J=11.4 Hz, 1H), 2.30 (dd, J=3.9 and 12.3 Hz, 1H), 2.45-2.60 (m, 3H), 2.81 (bd, J=11.4 Hz, 1H), 2.98 (bd, J=11.1 Hz, 1H), 3.65-3.85 (m, 2H), 7.14 (d, J=7.2 Hz, 2H), 7.20 (d, J=6.9 Hz, 1H), 7.28 (t, J=7.2 Hz, 2 H; MS (m/z) 249, 232, 218, 188, 91. Anal. Calcd for C15H23NO2: C, 72.25; H, 9.30; N, 5.62. Found C, 72.19; H, 9.43; N, 5.75.

Workup

  1. concentrationthen was concentrated in vacuo
  2. dissolutionThe resulting crude product was dissolved in water (50 mL)
  3. washwashed with ether (20 mL)
  4. extractionextracted with CH2Cl2 (3×30 mL)
  5. customThe crude compound was purified by trituration with EtOAc (5 mL) for 2 h

Sources & evidence

ORD record
ord-3bca5749848448d5befc36a6568faf72
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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