Acetyl chloride → N,N-Diethyl-4-[3-acetoxyphenyl(1-propylpiperidin-4-yl)amino]benzamide Hydrochloride

HRID 2304535Notes

Reaction equation

HRID 2304535 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)[CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].[C:31]([Cl:34])(=[O:33])[CH3:32]>C(Cl)Cl>[ClH:34].[CH2:29]([N:3]([CH2:1][CH3:2])[C:4](=[O:28])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:31](=[O:33])[CH3:32])[CH:22]=2)[CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]2)=[CH:9][CH:10]=1)[CH3:30]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 9811538N,N-diethyl-4-[3-hydroxyphenyl(1-propylpiperidin-4-yl)amino]benzamide

Product 1

HCID 18435758N,N-Diethyl-4-[3-acetoxyphenyl(1-propylpiperidin-4-yl)amino]benzamide HydrochlorideYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.96 g (2.3 mmol) of N,N-diethyl-4-[3-hydroxyphenyl(1-propylpiperidin-4-yl)amino]benzamide was stirred in 20 mL of CH2Cl2 and 0.17 mL of acetyl chloride was added. The mixture was stirred for 2 h. The solvent was evaporated and the residue recrystallized from 2-PrOH to give 0.7 g (62% yield) of the title compound as a white crystalline solid: mp 218-219° C. MS m/z=452 (M++H). 300 MHz 1H NMR (DMSO-d6) δ7.3 (d 2H); 7.2 (m, 1H);6.9 (d, 2H);6.7 (m, 2H);4.1 (t, 3H); 3.6 (d, 2H); 3.4 (m, 4H); 2.8 (m, 4H); 2.4(m, 2H); 2.2(s, 3H) 2.1 (d, 2H); 1.9 (m, 2H); 1.2 (t, 6H), 1.0 (t, 3H). Anal calcd. for C27H37N3O3.HCl: C, 66.45; H, 7.45; N, 8.61. Found: C, 66.07; H, 7.83; N, 8.32.

Workup

  1. customThe solvent was evaporated
  2. customthe residue recrystallized from 2-PrOH

Sources & evidence

ORD record
ord-9b884d4abde1468e9759ee6366a4c90c
Source dataset
uspto-grants-2002_08
Patent number
US06436959B1

Reaction notes

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