p-Anisoyl chloride → Encainide hydrochloride

HRID 2292047Notes

Reaction equation

HRID 2292047 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[CH3:12].[C:17]([Cl:27])(=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1>CC(C)=O>[CH3:12][N:7]1[CH:6]([CH2:5][CH2:4][C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[NH:1][C:17]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)=[O:26])[CH2:11][CH2:10][CH2:9][CH2:8]1.[ClH:27]

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 110852822-(2-Aminophenethyl)-1-methylpiperidine

Product 1

HCID 48040Encainide hydrochlorideYield 60.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Unpurified 2-(2-aminophenethyl)-1-methylpiperidine (II; 14.3 g, 0.066 moles) was dissolved in 100 mL dry acetone and p-anisoyl chloride (12.1 g, 0.071 mole) was added. The reaction mixture was stirred for 16 hours, cooled to 5°, and filtered. The solid material was washed with 25 mL of cold acetone and dried in vacuo at 25° for 6 hours. The dried solid was recrystallized from isopropanol-methanol to give 15.5 g of encainide hydrochloride, m.p. 183-185°.

Workup

  1. temperaturecooled to 5°
  2. filtrationfiltered
  3. washThe solid material was washed with 25 mL of cold acetone
  4. customdried in vacuo at 25° for 6 hours
  5. customThe dried solid was recrystallized from isopropanol-methanol

Sources & evidence

ORD record
ord-4f74b82ce4f64ed2b5a656c9c1252e78
Source dataset
uspto-grants-1989_01
Patent number
US04800226

Reaction notes

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