4-Amino-5-chloro-2-methoxybenzoic acid → 2,3-methylenedioxy-N-[(4-benzyl-2-morpholinyl)methyl]benzamide

HRID 1608193Notes

Reaction equation

HRID 1608193 reaction equation
[NH2:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1.[CH2:16]1[O:27][C:26]2[C:18](=[C:19]([CH:23]=[CH:24][CH:25]=2)[C:20](O)=[O:21])[O:17]1.NCC1OCCN(CC2C=CC(C#N)=CC=2)C1.NC1C(Cl)=CC(C(O)=O)=C(OC)C=1>>[CH2:16]1[O:27][C:26]2[C:18](=[C:19]([CH:23]=[CH:24][CH:25]=2)[C:20]([NH:1][CH2:2][CH:3]2[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:4]2)=[O:21])[O:17]1

Participants

5

Reactant 4

HCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 3048321,3-Dioxaindane-4-carboxylic acidHCID 2776360(4-Benzylmorpholin-2-yl)methanamineHCID 148818422-Aminomethyl-4-(4-cyanobenzyl)morpholine

Product 1

HCID 148818502,3-methylenedioxy-N-[(4-benzyl-2-morpholinyl)methyl]benzamide

Procedure

The title compound is prepared in substantially the same manner as in Example 6(1), using 2-aminomethyl-4-benzylmorpholine and 2,3-methylenedioxybenzoic acid, respectively, in place of 2-aminomethyl-4-(4-cyanobenzyl)morpholine and 4-amino-5-chloro-2-methoxybenzoic acid in Example 6(1). The free base thus obtained is treated in substantially the same manner as in Example 6(2) to give the fumarate 1/4 hydrate of the title compound, mp 144°-146° C. (recrystallized from ethanol).

Workup

  1. customThe free base thus obtained
  2. additionis treated in substantially the same manner as in Example 6(2)
  3. customto give
  4. customthe fumarate 1/4 hydrate of the title compound, mp 144°-146° C. (recrystallized from ethanol)

Sources & evidence

ORD record
ord-8b7c2c4cf5884be5b322960a835cc7e3
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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