Chloroacetyl chloride → N-((1-benzyl-4-hydroxypiperidin-4-yl)methyl)-2-chloroacetamide

HRID 876050Notes

Reaction equation

HRID 876050 reaction equation
[NH2:1][CH2:2][C:3]1([OH:16])[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1.C(N(CC)CC)C.[Cl:24][CH2:25][C:26](Cl)=[O:27]>ClCCl.O>[CH2:9]([N:6]1[CH2:7][CH2:8][C:3]([CH2:2][NH:1][C:26](=[O:27])[CH2:25][Cl:24])([OH:16])[CH2:4][CH2:5]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 104210264-(Aminomethyl)-1-benzylpiperidin-4-ol

Product 1

HCID 52911160N-((1-benzyl-4-hydroxypiperidin-4-yl)methyl)-2-chloroacetamideYield 78.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 397 (39.7 g, 180 mmol) in dichloromethane (350 mL) was added triethylamine (50.0 mL, 359 mmol), followed by dropwise addition of chloroacetyl chloride (16.5 mL, 207 mmol) over 15 minutes. The resulting solution was stirred at room temperature for 1.25 hours. The crude mixture was diluted with DCM and water, and extracted with DCM twice. The combined organics were dried over Na2SO4 and concentrated in vacuo to give compound 398 (41.9 g, 78%). LCMS-ESI (POS), M/Z, M+1: Found 297.1, Calculated 297.1.

Workup

  1. extractionextracted with DCM twice
  2. dry with materialThe combined organics were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a822be1c7228479387f6cb50fb77ecc5
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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