p-Anisoyl chloride → Encainide hydrochloride

HRID 653198Notes

Reaction equation

HRID 653198 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 5o, and filtered. The solid material was washed with 25 mL of cold acetone and dried in vacuo at 25o 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. filtrationfiltered
  2. washThe solid material was washed with 25 mL of cold acetone
  3. dry with materialdried in vacuo at 25o for 6 hours
  4. customThe dried solid was recrystallized from isopropanol-methanol

Sources & evidence

ORD record
ord-2ffbfa7abcb14a3693f65e71f3979221
Source dataset
uspto-grants-1987_06
Patent number
US04675409

Reaction notes

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