Pyridine → Acetamide, N-(1-adamantyl)-2-chloro-

HRID 492135Notes

Reaction equation

HRID 492135 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]12([NH2:16])[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.N1C=CC=CC=1>C(OCC)C>[C:6]12([NH:16][C:3](=[O:4])[CH2:2][Cl:1])[CH2:13][CH:12]3[CH2:11][CH:10]([CH2:9][CH:8]([CH2:14]3)[CH2:7]1)[CH2:15]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 2130AmantadineHCID 6577Chloroacetyl chloride

Product 1

HCID 64161Acetamide, N-(1-adamantyl)-2-chloro-Yield 34.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of chloroacetyl chloride (1.6 mL, 20 mmol) in anhydrous diethyl ether (10 mL) was added dropwise within 5 min to a solution of 1-adamantanamine (3.0 g, 20 mmol) and pyridine (1.63 mL, 20 mmol) in anhydrous diethyl ether (40 mL) at 0° C. The yellow suspension was stirred for 1 h at that temperature. The precipitate was removed by filtration and washed by diethyl ether (10 mL). The combined organic solution was washed with HCl (2 N, 2×15 mL), followed by sat. NaHCO3 (15 mL), sat. NaCl (15 mL) solutions and dried with Na2SO4. The solvent was removed at reduced pressure and the residue was recrystallized from diethyl ether-hexanes to afford N-(1-adamantyl)chloroacetamide (1.551 g, 34%) as a yellow solid.

Workup

  1. customThe precipitate was removed by filtration
  2. washwashed by diethyl ether (10 mL)
  3. washThe combined organic solution was washed with HCl (2 N, 2×15 mL)
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed at reduced pressure
  6. customthe residue was recrystallized from diethyl ether-hexanes

Sources & evidence

ORD record
ord-c30a954ac9a14522a94ef6c7c36d3eb9
Source dataset
uspto-grants-2009_05
Patent number
US07531662B2

Reaction notes

Loading…