Metoclopramide → HCID 14372589, compound

HRID 620280

Reaction equation

HRID 620280 reaction equation
NC1C(Cl)=CC(C(NCCN(CC)CC)=O)=C(OC)C=1.[NH2:21][C:22]1[C:49]([Cl:50])=[CH:48][C:25]([C:26]([NH:28][C@H:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][CH2:37][O:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[CH2:31][C@H:30]2[O:46][CH3:47])=[O:27])=[C:24]([O:51]C)[CH:23]=1>>[NH2:21][C:22]1[C:49]([Cl:50])=[CH:48][C:25]([C:26]([NH:28][C@H:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][CH2:37][O:38][C:39]3[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=3)[CH2:31][C@H:30]2[O:46][CH3:47])=[O:27])=[C:24]([OH:51])[CH:23]=1

Participants

3

Reactant 2

HCID 4168MetoclopramideHCID 53110474-amino-5-chloro-N-[(3R,4S)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide

Product 1

HCID 14372589HCID 14372589, compoundYield 54%

Procedure

The general procedure of Preparation No. 1 was repeated except that the 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide utilized therein was replaced by cis-4-amino-5-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-methoxybenzamide (2 g, 4.3 mmoles) [prepared according to the procedure described in published European patent application No. 76,530 (1983)]. The product was crystallized from 2-propanol to give the title product in 54% yield, mp. 146°-148° C.

Workup

  1. customThe general procedure of Preparation No
  2. customprepared
  3. customThe product was crystallized from 2-propanol

Sources & evidence

ORD record
ord-ff7159e3f7004be99e9b9669c47034ab
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Linked notes

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