Nicotinamide → Declopramide hydrochloride

HRID 51158

Reaction equation

HRID 51158 reaction equation
CCN(CCNC(C1C=CC(N)=CC=1)=O)CC.CCN(CCNC(C1C=CC(N)=C([Cl:35])C=1)=O)CC.[CH3:36][CH2:37][N:38]([CH2:41][CH2:42][NH:43][C:44]([C:46]1[CH:47]=[C:48]([Cl:55])[C:49]([NH2:54])=[CH:50][C:51]=1OC)=[O:45])[CH2:39][CH3:40].C(N)(=O)C1C=CC=NC=1.C(N(CC)CCC1N=CC=CC=1C(N)=O)C>>[ClH:35].[CH2:39]([N:38]([CH2:37][CH3:36])[CH2:41][CH2:42][NH:43][C:44](=[O:45])[C:46]1[CH:51]=[CH:50][C:49]([NH2:54])=[C:48]([Cl:55])[CH:47]=1)[CH3:40]

Participants

6

Reactant 5

HCID 936NicotinamideHCID 4168MetoclopramideHCID 4913ProcainamideHCID 70177DeclopramideHCID 867594092-Diethylamino-ethyl nicotinamide

Product 1

HCID 22737404Declopramide hydrochloride

Procedure

Reaction of aryl carboxamides with radiation. Aqueous 100 μM solutions of procainamide (4-amino-N-(2-diethylamino-ethyl)benzamide), 3-chloro-procainamide (N-(2-diethylamino-ethyl)-4-amino-3-chlorobenzamide), metoclopramide (4-amino-5-chloro-N-(2-diethylamino-ethyl)-2-methoxybenzamide), nicotinamide and N-(2-diethylamino-ethyl nicotinamide were given 1000 Gy of irradiation from 137cesium source (1.3 Gy/min., Scanditronix) at room temperature for 30 min. The various reaction mixtures were then vacuum evaporated to dryness, redissolved in methanol, spotted on silica gel 60 F245 thin layer chromatography (TLC) plates in 1-butanol:acetic acid:water (4:1:1, v/v/v), and visualized with short and long wave ultraviolet light and also in an iodine chamber, and the Rf values calculated in the conventional manner.

Workup

  1. custom1000 Gy of irradiation from 137cesium source (1.3 Gy/min., Scanditronix) at room temperature for 30 min
  2. customThe various reaction mixtures
  3. customvacuum evaporated to dryness
  4. dissolutionredissolved in methanol

Sources & evidence

ORD record
ord-9c1b669486164a30b677ea76a206c449
Source dataset
uspto-grants-2004_03
Patent number
US06713517B1

Linked notes

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