Water → Benzyl 2-(4-hydroxypiperidin-1-yl)acetate

HRID 58893Notes

Reaction equation

HRID 58893 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.Br[CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C(N(CC)CC)C.O>ClCCl>[OH:7][CH:4]1[CH2:5][CH2:6][N:1]([CH2:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62576Benzyl bromoacetateHCID 79341Piperidin-4-ol

Product 1

HCID 21805034Benzyl 2-(4-hydroxypiperidin-1-yl)acetateYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To piperidin-4-ol (HCl salt, 9.0 g) was added a solution of benzyl 2-bromoacetate (15.0 g, 65.7 mmol) in dichloromethane (100 mL). The mixture was cooled to 0° C. and triethylamine (27.6 mL, 0.200 mol) was added. The reaction mixture was allowed to warm to ambient temperature and stirred for 2 h. Water (100 mL) was added and the resulting mixture was extracted with dichloromethane (100 mL×3). The organic extracts were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=20:1 to 10:1) to afford benzyl 2-(4-hydroxypiperidin-1-yl)acetate (8.3 g, 51% yield).

Workup

  1. temperatureto warm to ambient temperature
  2. extractionthe resulting mixture was extracted with dichloromethane (100 mL×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=20:1 to 10:1)

Sources & evidence

ORD record
ord-ec3130047fd144068202289247756349
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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